3-hydroxymethyl-thiophene
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane Ambient temperature; | 96% |
With oxygen In 1,3,5-trimethyl-benzene at 60℃; under 760.051 Torr; for 3h; Solvent; Reagent/catalyst; | 95% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium nitrate; europium(III) nitrate hexahydrate; acetic acid In toluene at 40℃; for 9h; | 95% |
2,5-dihydro-3-thiophenecarboxaldehyde
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With sulfuryl dichloride In dichloromethane at -36 - -30℃; for 0.5h; | 92% |
With sulfuryl dichloride In dichloromethane at -35℃; | 58.9% |
2-(thiophen-3-yl)-1,3-dithiane
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With eosin y In water; acetonitrile at 20℃; for 3h; Irradiation; | 89% |
3-Bromothiophene
N,N-dimethyl-formamide
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-Bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78 - 20℃; for 1.5h; | 87.8% |
Stage #1: 3-Bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at 20℃; for 12h; Inert atmosphere; | 70% |
3-hydroxymethyl-thiophene
A
3-thiophene carboxaldehyde
B
3-Thiophene carboxylic acid
Conditions | Yield |
---|---|
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 87.5% B 0.1% |
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h; Schlenk technique; | A 18 %Spectr. B 65% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 52.3% B 2.3% |
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane In tetrahydrofuran for 1h; Reagent/catalyst; Fukuyama Reduction; | 87% |
Conditions | Yield |
---|---|
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h; | 84% |
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave; | 68% |
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; formic acid In N,N-dimethyl-formamide at 50℃; under 760 Torr; for 5h; Electrolysis; | 82 % Chromat. |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube; | 84% |
Stage #1: 3-thienyl iodide; formic acid With palladium diacetate; acetic anhydride; tricyclohexylphosphine In N,N-dimethyl-formamide at 30℃; for 1h; Inert atmosphere; Green chemistry; Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Green chemistry; | 65% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere; | 82% |
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h; | 82 % Chromat. |
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h; | 82 % Chromat. |
With N,N,N,N,-tetramethylethylenediamine; C6H6*C48H78O2P2Pd; hydrogen In toluene at 20 - 100℃; under 3750.38 Torr; Inert atmosphere; Autoclave; | 87 %Chromat. |
Conditions | Yield |
---|---|
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 82% |
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave; | 60% |
A
3-thiophene carboxaldehyde
B
3-hydroxymethyl-thiophene
Conditions | Yield |
---|---|
In methanol decomposition of the complex by refluxing in methanol under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compounds with ether, gas chromatography; | A 19% B 81% |
Conditions | Yield |
---|---|
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 80% |
3-Bromothiophene
dicobalt octacarbonyl
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 60℃; for 16h; Schlenk technique; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere; | 70% |
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 48h; | 73 % Spectr. |
Multi-step reaction with 2 steps 1: 88 percent / LiAlH4 / diethyl ether 2: 7.3 g / PCD / CH2Cl2 / 1.5 h View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride 2: pyridine 3: phosphorus (V)-chloride; benzene / anschliessend in Aether mit Zinn(II)-chlorid und Chlorwasserstoff behandeln und Erhitzen des vom Aether befreiten Reaktionsgemisches mit Wasser View Scheme |
3-Bromothiophene
3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane; palladium diacetate; sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 80℃; Inert atmosphere; Sealed tube; | 70% |
3-styryl-thiophene
A
3-thiophene carboxaldehyde
B
naphtho[1,2-b]thiophene
C
benzaldehyde
D
[2,2']Bi[naphtho[1,2-b]thiophenyl]
Conditions | Yield |
---|---|
With oxygen In hexane Cyclization; oxidation; Irradiation; | A 8% B 69% C 8% D 15% |
With oxygen In hexane at 25℃; Cyclization; oxidation; Irradiation; | A 8% B 69% C 8% D 15% |
Conditions | Yield |
---|---|
With diethylamine at 70℃; for 6h; Temperature; Reagent/catalyst; | 65% |
Conditions | Yield |
---|---|
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 19h; chemoselective reaction; | 64% |
3-thienyl iodide
carbon dioxide
A
thiophene
B
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With palladium on activated charcoal; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 20h; Autoclave; | A 27% B 64% |
Conditions | Yield |
---|---|
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave; | 63% |
Conditions | Yield |
---|---|
With sodium azide; copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 100℃; for 10h; Schlenk technique; Sealed tube; | A 47% B 53% |
3-Bromomethylthiophene
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
28% | |
With chloroform; hexamethylenetetramine Erhitzen des Reaktionsprodukts mit Wasserdampf oder mit wss. Aethanol; | |
Multi-step reaction with 2 steps 1: chloroform 2: water / Heating View Scheme | |
With 4-methylmorpholine N-oxide In ethyl acetate at 50℃; for 6h; Solvent; |
Conditions | Yield |
---|---|
1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 10℃; for 2h; | 23% |
N-phenyl-3-thiophene-carboxamide
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With phosphorus pentachloride; benzene anschliessend in Aether mit Zinn(II)-chlorid und Chlorwasserstoff behandeln und Erhitzen des vom Aether befreiten Reaktionsgemisches mit Wasser; |
methyllithium
thieno(3,2-d) isoselenazole
A
3-thiophene carboxaldehyde
D
2-Methylselanyl-thiophene-3-carbaldehyde
Conditions | Yield |
---|---|
With water In tetrahydrofuran; diethyl ether at -80℃; for 5h; Product distribution; | A 16 % Chromat. B 18 % Chromat. C 26 % Chromat. D 100 % Chromat. |
(3-thienyl)diazomethane
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With oxygen In solid matrix at -233.2℃; |
Conditions | Yield |
---|---|
With oxygen; 9,10-Dicyanoanthracene In acetonitrile at 25℃; for 3h; Oxidation; Irradiation; | A 100 % Turnov. B 100 % Turnov. |
3-thiophene carboxaldehyde
diethoxyphosphoryl-acetic acid ethyl ester
(E)-3-thiophen-3-yl-acrylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; for 1h; | 100% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.25h; | 100% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In tetrahydrofuran at 20℃; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 90℃; for 0.5h; | 90% |
3-thiophene carboxaldehyde
O,O-diethyl benzylphosphonate
(E)-3-styrylthiophene
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide at 0 - 20℃; for 1.75h; | 100% |
3-thiophene carboxaldehyde
(R)-Phenylglycinol
(R)-2-Phenyl-2-{[1-thiophen-3-yl-meth-(E)-ylidene]-amino}-ethanol
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
In benzene Heating; | 92% |
Conditions | Yield |
---|---|
With aluminum oxide for 12h; | 100% |
3-thiophene carboxaldehyde
trimethyl phosphonoacetate
3-Thiophen-3-yl-acrylic Acid Methyl Ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; | 100% |
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran for 1h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 20℃; for 18h; | 94% |
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; | 81% |
3-thiophene carboxaldehyde
(α-chloro-benzyl)-phosphonic acid diphenyl ester
1-phenyl-2-(3-thienyl)ethyne
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; (α-chloro-benzyl)-phosphonic acid diphenyl ester With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.; | 100% |
3-thiophene carboxaldehyde
diphenyl chloro(4-methoxycarbonylphenyl)methylphosphonate
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; diphenyl chloro(4-methoxycarbonylphenyl)methylphosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; diphenyl phosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.; | 100% |
3-thiophene carboxaldehyde
Diphenyl 1-Chloro-1-(4-pyridyl)methanephosphonate
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; diphenyl 1-chloro-1-(4-pirydyl)methanephosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Horner-Emmons reaction; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction; Further stages.; | 100% |
3-thiophene carboxaldehyde
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 18h; | 100% |
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃; for 2h; | 90% |
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃; for 2h; | 90% |
3-thiophene carboxaldehyde
malonic acid dimethyl ester
dimethyl [(3-thienyl)methylene]malonate
Conditions | Yield |
---|---|
With piperidine; benzoic acid for 12h; Heating / reflux; | 100% |
With piperidine; acetic acid In benzene for 4h; Reflux; | 96% |
With piperidine; acetic acid In benzene Dean-Stark; Reflux; |
3-thiophene carboxaldehyde
4-phenyl-1-piperazine
1-phenyl-4-(thiophen-3-ylmethyl)piperazine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 2h; Solvent; Green chemistry; | 100% |
Conditions | Yield |
---|---|
In ethanol at 80℃; Inert atmosphere; | 100% |
3-thiophene carboxaldehyde
3-thiophenecarboxaldehyde oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In pyridine; water; ethyl acetate | 99% |
With hydroxylamine | |
With hydroxylamine hydrochloride; copper(II) sulfate at 90℃; for 2h; | 85 % Spectr. |
With hydroxylamine In methanol | |
With sodium chloride; hydroxylamine hydrochloride; sodium carbonate In ethanol; water |
Conditions | Yield |
---|---|
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With lithium hydroxide In ethanol at 20℃; for 0.166667h; Large scale; Stage #2: 3-thiophene carboxaldehyde In ethanol at 20℃; Large scale; | 99% |
With sodium hydroxide In ethanol; water |
3-thiophene carboxaldehyde
trimethylsilylacetylene
1-(thiophen-3-yl)-3-(trimethylsilyl)prop-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 0℃; for 1h; | 99% |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 0℃; for 1h; | 95% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; |
Conditions | Yield |
---|---|
With 1-hexyl-3-methylimidazolium hydrogen sulphate In ethanol at 20℃; for 1h; | 99% |
3-thiophene carboxaldehyde
ethylene glycol
2-(thiophen-3-yl)-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 165℃; for 6h; | 99% |
With toluene-4-sulfonic acid In benzene Heating; | 97% |
toluene-4-sulfonic acid In toluene for 4h; Heating / reflux; | 95.9% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 3h; Heating; | 99% |
3-thiophene carboxaldehyde
methylmagnesium bromide
1-(thiophen-3-yl)ethan-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 2h; | 99% |
Conditions | Yield |
---|---|
In ethanol at 21℃; Inert atmosphere; | 99% |
In ethanol Heating; sonication; | 79% |
3-thiophene carboxaldehyde
nitromethane
(S)-(+)-2-nitro-1-(thiophen-3-yl)ethanol
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine; N-<(1S,2R,4R)-1,7,7-trimethylbicyclo<2.2.1>hept-2-yl>-1-(2-pirydyl)methanamine In ethanol at -50℃; Henry reaction; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 80℃; for 24h; Molecular sieve; | 99% |
3-thiophene carboxaldehyde
5-hydroxy-4,6-dimethyl-3-heptanone
Conditions | Yield |
---|---|
With samarium diiodide; benzaldehyde In tetrahydrofuran at -15℃; for 1h; Evans-Tishchenko coupling reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction; | 99% |
3-thiophene carboxaldehyde
2-bromo-5-methoxy-benzaldehyde
2-bromo-5-methoxybenzyl thiophene-3-carboxylate
Conditions | Yield |
---|---|
With 4-tert-butylbenzyl mercaptan; dibutylmagnesium In tetrahydrofuran at 65℃; for 24h; Tishchenko-Claisen Dismutation; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
In toluene at 130℃; Solvent; Temperature; Inert atmosphere; Molecular sieve; | 99% |
3-thiophene carboxaldehyde
1,1,3‐tribromo‐2,2‐dimethylcyclopropane
Conditions | Yield |
---|---|
Stage #1: 1,1,3‐tribromo‐2,2‐dimethylcyclopropane With n-butyllithium In diethyl ether; hexane at -78 - -10℃; for 1h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In diethyl ether; hexane at -50 - -10℃; for 0.25h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; tryptamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.0333333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; | 99% |
Conditions | Yield |
---|---|
With FeBr2*2THF; C30H46N4Si2(2+) In acetonitrile at 20℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With potassium ethoxide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 99% |
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