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methyl 5-hydroxypentanoate
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With oxalyl dichloride; triethylamine In dichloromethane; dimethyl sulfoxide at -78 - 0℃; for 0.833333h; stereoselective reaction; | 99% |
Stage #1: methyl 5-hydroxypentanoate With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Swern oxidation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; Swern oxidation; Inert atmosphere; Stage #3: With water; ammonium chloride In dichloromethane | 95% |
Stage #1: methyl 5-hydroxypentanoate With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Stage #2: With triethylamine In dichloromethane at -78℃; | 95% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal | 95% |
With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal In tetrahydrofuran | 77% |
With triethylsilane; palladium on activated charcoal for 1h; Ambient temperature; | 72% |
Conditions | Yield |
---|---|
Stage #1: methanol; cyclopentene With sodium hydrogencarbonate; ozone In dichloromethane at -78℃; Stage #2: With acetic anhydride; triethylamine In dichloromethane at 0℃; for 4.25h; Inert atmosphere; | 95% |
With oxygen; sodium hydrogencarbonate; ozone In dichloromethane at -78℃; | 92% |
Stage #1: methanol; cyclopentene With sodium hydrogencarbonate; ozone In dichloromethane at -78℃; Stage #2: With acetic anhydride; triethylamine In dichloromethane; benzene for 4h; | 89% |
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 0.5h; oxidative cleavage; | 91% |
Conditions | Yield |
---|---|
With potassium osmate(VI); sodium periodate In tetrahydrofuran; water at 20℃; for 3h; | 76% |
With potassium osmate(VI) dihydrate; sodium periodate In tetrahydrofuran; water at 20℃; for 3h; | 59% |
With sodium periodate; potassium osmate monohydrate In tetrahydrofuran; water at 20℃; for 3h; | |
Stage #1: methyl 5-hexenoate With ozone In dichloromethane at -78℃; for 1h; Stage #2: With dimethylsulfide In dichloromethane at -78 - 20℃; |
methyl 4-(N,N-diethylcarbamoyl)butyrate
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With Schwartz's reagent for 0.25h; | 74% |
Conditions | Yield |
---|---|
With pyridine; ozone In methanol for 2h; Ring cleavage; | 68% |
With ozone In methanol at -78℃; | 34% |
With dimethylsulfide; ozone In methanol at -78℃; |
Conditions | Yield |
---|---|
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With triethylamine at 20℃; for 18h; Stage #2: With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine at 20℃; for 14h; | 65% |
With sulfuric acid; pyridinium chlorochromate 1) reflux, 5 h, 2) CH2Cl2,, 23 deg C, 2 h; Yield given. Multistep reaction; | |
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid at 70℃; for 5h; Stage #2: With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; Further stages.; | |
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid for 12h; Reflux; Stage #2: With pyridinium chlorochromate In dichloromethane at 29℃; for 5h; | |
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid Reflux; Stage #2: With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #3: With triethylamine In dichloromethane; dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
Stage #1: cyclopentene With sodium hydrogencarbonate; ozone In methanol; dichloromethane; benzene at 78℃; Stage #2: acetic anhydride With triethylamine In methanol; dichloromethane; benzene at 0℃; for 4h; Inert atmosphere; | 60% |
With oxygen; sodium hydrogencarbonate; ozone; triethylamine 1.) CH2Cl2, CH3OH, -70 deg C, 1.34 h, 2.) CH2Cl2, CH3OH, a) -20 deg C, 5 h, b) 8 deg C, 15 h; Yield given. Multistep reaction; |
diazomethane
cyclopentene
A
methyl 4-formylbutanoate
B
Dimethyl glutarate
C
Glutaraldehyde
Conditions | Yield |
---|---|
Stage #1: cyclopentene With ozone In dichloromethane at -78℃; Stage #2: With Merrifield resin-bound piperidine In dichloromethane at 20℃; for 24h; Stage #3: diazomethane In dichloromethane; ethyl acetate | A 59% B 14% C 23% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 20℃; for 2h; Ring cleavage; methylation; | 52% |
Conditions | Yield |
---|---|
With disodium hydrogenphosphate In dimethyl sulfoxide at 150℃; for 0.166667h; | 43% |
[bis(acetoxy)iodo]benzene
5-(4-methoxycarbonylbutyl)-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodide
A
methyl 4-formylbutanoate
B
1,4-Diphenyl-3-methylmercapto-1,2,4-triazolium iodide
Conditions | Yield |
---|---|
With iodine; sodium methylate; potassium iodide 1.) CHCl3, reflux, 30 min, 2.) MeOH, room temp, 15 min; Yield given. Multistep reaction; | A n/a B 35% |
2-hydroxy-2-cyclohexen-1-one
A
1,5-pentanedioic acid
B
5-oxopentanoic acid
C
methyl 4-formylbutanoate
D
methyl 5-methoxycarbonyl-2-hydroxypentanoate
E
methyl 5-carboxy-2-hydroxypentanoate
F
2-Oxo-hexanedioic acid dimethyl ester
Conditions | Yield |
---|---|
With oxygen; CuCl2*2H2O In methanol at 25℃; under 760 Torr; for 5h; Mechanism; various 1,2-cyclohexanediones; | A n/a B 8% C 5% D 12% E 8% F 3% |
2,2-dimethoxy-3,4-dihydropyrane
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With hydrogenchloride | |
With oxonium; sodium chloride In dichloromethane for 8h; Ambient temperature; pH= 4; Yield given; |
Conditions | Yield |
---|---|
With hydrogen; Rh catalyst at 150℃; |
Conditions | Yield |
---|---|
With methanol; hydrogen cation; pyridinium chlorochromate 2.) CH2Cl2; Yield given. Multistep reaction; | |
With swern reagent Multistep reaction; | |
Multi-step reaction with 2 steps 1: (COCl)2; DMSO; Et3N View Scheme |
Conditions | Yield |
---|---|
With dimethylsulfide; sodium methylate; ozone 1.) -78 deg C, 2.) -78 deg C, 3.) 1h; Yield given. Multistep reaction; |
valeric acid
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With pyridinium chlorochromate Multistep reaction; |
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With acetic anhydride; triethylamine for 24h; Ambient temperature; Yield given; |
(8Z,11Z,14Z)-5,6-Dihydroxy-icosa-8,11,14-trienoic acid methyl ester
A
methyl 4-formylbutanoate
B
(3Z,6Z,9Z)-pentadeca-3,6,9-trienal
Conditions | Yield |
---|---|
With lead(IV) acetate In dichloromethane at 78℃; for 0.333333h; |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate; magnesium sulfate 1.) reflux, 8 h, 2.) H2O, room temperature, 12 h; Yield given. Multistep reaction; |
methyl 5,5-dimethoxyvalerate
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; water In tetrahydrofuran at 17 - 22℃; for 5h; |
hydrogenchloride
2,2-dimethoxy-3,4-dihydropyrane
methyl 4-formylbutanoate
methanol
cyclopentene
A
2-methoxy-3,4-dihydro-2H-pyran
B
methyl 4-formylbutanoate
C
methyl 5,5-dimethoxyvalerate
D
Dimethyl glutarate
E
1,1,5,5-tetramethoxy-pentane
F
Glutaraldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; ozone Product distribution; Mechanism; -78 deg to r.t.; | A n/a B 2 % Chromat. C 46 % Chromat. D 23 % Chromat. E 27 % Chromat. F 1 % Chromat. G n/a |
5,6-Epoxyeicosatrienoic acid methyl ester
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) 10:1 formic acid-acetic anhydride; 2) sodium methoxide / 1) 12h, 25 deg C; 2) methanol, 2h, 25 deg C 2: lead tetraacetate / CH2Cl2 / 0.33 h / 78 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2.) SOCl2 2: reduction View Scheme |
methyl but-3-enoate
carbon monoxide
A
methyl 4-formylbutanoate
B
3-formyl-butyric acid methyl ester
Conditions | Yield |
---|---|
With hydrogen; acetic acid; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran at 40℃; under 7500.75 Torr; for 4h; Title compound not separated from byproducts.; | |
With dicarbonyl(acetylacotonato)rhodium(I); C59H50N4O2P2 In dichloromethane at 40℃; for 24h; regioselective reaction; | |
With acetylacetonatodicarbonylrhodium(l); [(C6H5)2PC6H4CONHC6H3C2NH(CH3)]2CH(C2H5); hydrogen; triethylamine In dichloromethane at 40℃; under 15001.5 Torr; for 24h; Autoclave; Schlenk technique; Inert atmosphere; regioselective reaction; |
methyl 4-formylbutanoate
L-cysteine ethyl ester hydrochloride
(R)-2-(3-Methoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With magnesium sulfate; potassium carbonate In toluene Ambient temperature; | 100% |
methyl 4-formylbutanoate
(E)-isopropyl 4-(4-chlorophenyl)-2-oxobut-3-enoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition; | 99% |
methyl 4-formylbutanoate
(E)-isopropyl 4-(2-fluorophenyl)-2-oxobut-3-enoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition; | 99% |
methyl 4-formylbutanoate
pent-3-yn-1-yltriphenylphosphonium iodide
(Z)-dec-5-en-8-ynoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 3h; Wittig Olefination; Reflux; stereoselective reaction; | 99% |
methyl 4-formylbutanoate
thiophenol
5,5-bis-phenylsulfanyl-pentanoic acid methyl ester
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -50℃; for 0.5h; | 98% |
methyl 4-formylbutanoate
benzyl 2-oxo-4-phenylbut-3-enoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition; | 98% |
methyl 4-formylbutanoate
tert-Butyldimethyl(prop-2-ynyloxy)silane
Conditions | Yield |
---|---|
With copper(I) bromide In toluene at 25℃; for 24h; diastereoselective reaction; | 98% |
methyl 4-formylbutanoate
L-tryptophanol
(6S,12bR)-1,2,3,6,7,12b-hexahydro-6-(hydroxymethyl)indolo[2,3-a]quinolizin-4(12H)-one
Conditions | Yield |
---|---|
Stage #1: methyl 4-formylbutanoate; L-tryptophanol In toluene for 48h; Heating; Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 20h; Further stages.; | 95% |
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Reagent/catalyst; Time; Solvent; | 95% |
methyl 4-formylbutanoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition; | 95% |
methyl 4-formylbutanoate
(2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol
Conditions | Yield |
---|---|
In toluene Heating; | 94% |
methyl 4-formylbutanoate
(E)-isopropyl 4-(3-bromophenyl)-2-oxobut-3-enoate
Conditions | Yield |
---|---|
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition; | 94% |
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