Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With Dowex 50W×2 hydrogen form at 103 - 108℃; Reagent/catalyst; Autoclave; Large scale; | 98.6% |
With bis(acetylacetonato)dioxidomolybdenum(VI) for 8h; Heating; | 72% |
acrylic acid methyl ester
propanoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogen; palladium(II) complex of ferrocenylamine sulfide (2) In acetone under 4137.2 Torr; for 0.25h; or with catalyst 3, 0.75 h; | 100% |
With [Ir(1-(1′-methylpyrazole)-3-(4′-methylphenyl)triazenide)Cp*Cl]; isopropyl alcohol at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Glovebox; | 99% |
With tetrahydroxydiboron; water; sodium hydrogencarbonate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere; | 99% |
ethene
carbon monoxide
trans-[Pd(COEt)(OTs)(PPh3)2]
B
propanoic acid methyl ester
[Pd(COEt)(PPh3)3](TsO)
Conditions | Yield |
---|---|
at -80.16 - 49.84℃; under 3000.3 Torr; for 0.0133333h; | A 0.1% B 100% C n/a |
Conditions | Yield |
---|---|
With methanesulfonic acid; palladium diacetate; bis(phosphaadamantyl)diphosphine at 90℃; | 99% |
With α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium dichloride at 80℃; under 15001.5 - 22502.3 Torr; for 20h; Reagent/catalyst; Pressure; Inert atmosphere; Autoclave; | 99% |
With bis(acetylacetonato)palladium(II); 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); toluene-4-sulfonic acid at 80℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere; | 99% |
methanol
trans-[Pd(COEt)(OTs)(PPh3)2]
carbon monoxide
trans-[Pd(COOMe)(OTs)(PPh3)2]
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; triphenylphosphine In methanol Pd complex, (0.1 mmol) reacted with MeOH containing PPh3 (0.1 mmol) + p-toluenesulfonic acid (0.1 mmol) satd. with CO (ca. 20 min); pptd. with cold H2O; suspn. filtered; ppt. washed with cold H2O; dried (vac.); | A 90% B 99% |
Conditions | Yield |
---|---|
With palladium diacetate; toluene-4-sulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere; Autoclave; regioselective reaction; | 99% |
propionic acid
carbonic acid dimethyl ester
propanoic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry; | 98% |
With diiron nonacarbonyl at 180℃; for 1h; Sealed tube; |
Conditions | Yield |
---|---|
With tetrahydroxydiboron; water; sodium hydrogencarbonate In methanol at 80℃; for 12h; | 98% |
methanol
1,1'-(2-oxoimidazolidine-1,3-diyl)bis(propan-1-one)
A
imidazolidone
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
With C17H23BN2O at 50℃; under 760.051 Torr; for 15h; Inert atmosphere; chemoselective reaction; | A 97% B n/a |
methanol
1,1'-(2-oxoimidazolidine-1,3-diyl)bis(propan-1-one)
A
propanoic acid methyl ester
B
1-propionyl-2-oxo-imidazolidine
Conditions | Yield |
---|---|
With C17H23BN2O at 25℃; under 760.051 Torr; for 0.25h; Inert atmosphere; chemoselective reaction; | A n/a B 96% |
2-chloro-propionic acid methyl ester
propanoic acid methyl ester
Conditions | Yield |
---|---|
With sodium chloride; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating; further sodium halides or pseudo-halides and metal halides; | 95% |
With sodium hydrogensulfide; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating; | 95% |
With sodium iodide; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating; | 92% |
With sodium tetrahydroborate; tin(ll) chloride In tetrahydrofuran for 2h; Heating; | 90% |
Conditions | Yield |
---|---|
With ozone at -40℃; for 43h; | 92% |
Conditions | Yield |
---|---|
With ruthenium trichloride; tetraethylammonium iodide; bis(triphenylphosphine)iminium chloride In N,N-dimethyl-formamide at 165℃; under 18751.9 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Autoclave; | 85.4% |
With ruthenium trichloride; tetraethylammonium iodide In N,N-dimethyl-formamide at 190℃; under 45003.6 Torr; for 1h; Product distribution; var. solvents, reaction times, promoters, and ruthenium complexes, also in the presence of CO; | |
With tris(triphenylphosphine)ruthenium(II) chloride at 190 - 200℃; under 7500.6 Torr; for 18h; Product distribution; other alkyl formate; var. solvents, var. substrates concentrations; | |
With 1-butyl-1-methylpyrrolidinium chloride; dicobalt octacarbonyl; dichlorotricarbonylruthenium(II) dimer at 120℃; under 15001.5 Torr; for 15h; Product distribution / selectivity; |
propionic acid anhydride
A
propanoic acid methyl ester
B
1,8-diazabicyclo[5.4.0]undec-7-enium propanoate
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; | A 85% B n/a |
Dimethoxymethane
propionic acid anhydride
A
propanoic acid methyl ester
B
propionic acid methoxymethyl ester
Conditions | Yield |
---|---|
With Amberlyst 15 at 50 - 55℃; for 0.0833333h; Heating / reflux; | A n/a B 83.6% |
Conditions | Yield |
---|---|
With sodium carbonate; N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) at 20℃; for 40h; | 80% |
With magnesium hydroxide; oxygen at 90℃; under 2250.23 Torr; for 2h; |
acetic anhydride
2-Pentanone
A
propanoic acid methyl ester
B
butanoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; manganese(III) triacetate dihydrate at 90℃; under 3750.38 Torr; for 10h; Autoclave; | A 21% B 79% |
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform at 20℃; for 14h; Baeyer-Villiger oxidation; | A 14% B 78% |
With (η5-C5H4SiMe3)2NbH(O)C=CPh2 at 25℃; | |
With sec-decanepersulfonic acid In acetonitrile at 17℃; Rate constant; |
Conditions | Yield |
---|---|
With hydrogen In methanol at 220℃; under 37503.8 Torr; for 12h; Reagent/catalyst; | 77% |
With nickel(II) ferrite; hydrogen In methanol at 220℃; under 37503.8 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; | 75% |
trans-MeOIr(CO)(PPh3)2
acetaldehyde
A
HIr(PPh3)2(CO)2
B
acetic acid methyl ester
C
propanoic acid methyl ester
Conditions | Yield |
---|---|
In cyclohexane in dry box onto the degassed (vac.) soln. of complex (in a pressure tube fitted with a Teflon stopcock) CH3CHO distilled, 5 d reacted at room temp.; not isolated, spect. detection by IR and NMR in the soln.; | A n/a B 75% C n/a |
methanol
[hydroxy(tosyloxy)iodo]benzene
propionic acid anhydride
A
iodobenzene
B
propanoic acid methyl ester
C
methyl 2-{[(4-methylphenyl)sulfonyl]oxy}propanoate
Conditions | Yield |
---|---|
Stage #1: [hydroxy(tosyloxy)iodo]benzene; propionic acid anhydride at 100℃; for 0.333333h; Stage #2: methanol With toluene-4-sulfonic acid for 4h; Heating; | A n/a B n/a C 73% |
acrylic acid methyl ester
A
propanoic acid methyl ester
Conditions | Yield |
---|---|
In dichloromethane-d2 for 12h; Glovebox; Sealed tube; | A 28% B 72% |
Conditions | Yield |
---|---|
sulfuric acid Heating; | 70% |
methanol
carbon monoxide
ethylmercuric acetate
propanoic acid methyl ester
Conditions | Yield |
---|---|
With Wilkinson's catalyst at 65 - 100℃; under 5171.5 - 25857.4 Torr; | 66% |
methanol
propionic acid anhydride
(mesyloxyhydroxyiodo)benzene
A
iodobenzene
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: propionic acid anhydride; (mesyloxyhydroxyiodo)benzene at 100℃; for 0.333333h; Stage #2: methanol With toluene-4-sulfonic acid for 4h; Heating; | A n/a B n/a C 66% |
methanol
propionic acid anhydride
A
iodobenzene
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: propionic acid anhydride; {hydroxy[(+)-10-camphosulfonyloxy]iodo}benzene at 100℃; for 0.333333h; Stage #2: methanol With toluene-4-sulfonic acid for 4h; Heating; | A n/a B n/a C 62% |
Conditions | Yield |
---|---|
With hydrogen In methanol at 220℃; under 37503.8 Torr; for 12h; | A 10% B 60% |
methanol
methylpropioimidate hydrochloride
A
trimethoxypropane
B
propanoic acid methyl ester
Conditions | Yield |
---|---|
at 20℃; for 48h; | A 59% B n/a |
tri(o-tolyl)phosphonium tris(pentafluorophenyl)borohydride
acrylic acid methyl ester
A
propanoic acid methyl ester
Conditions | Yield |
---|---|
In dichloromethane-d2 for 12h; Glovebox; Sealed tube; | A 47% B 53% |
methyl pyrazine-2-carboxylate
propanoic acid methyl ester
methyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate
Conditions | Yield |
---|---|
Stage #1: methyl pyrazine-2-carboxylate With sodium hydride In toluene at 15 - 25℃; for 0.5h; Industrial scale; Stage #2: propanoic acid methyl ester In methanol; toluene at 15 - 40℃; Temperature; Solvent; Reagent/catalyst; Industrial scale; | 100% |
Stage #1: propanoic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl pyrazine-2-carboxylate In tetrahydrofuran at 0 - 25℃; for 3.5h; Stage #3: With ammonium chloride In tetrahydrofuran for 0.5h; | 89% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 5h; Inert atmosphere; | 79% |
With NaH; ammonium chloride In toluene |
propanoic acid methyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; | 99% |
Stage #1: propanoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1.33333h; Stage #2: (2R,6R)-6-[(methoxymethoxy)methyl]-1-(phenylmethyl)-2-[3-[[tris(1-methylethyl)silyl]oxy]propyl]-2-piperidinecarboxaldehyde In tetrahydrofuran; hexane at -78℃; for 0.75h; Aldol condensation; Stage #3: With ammonium chloride In tetrahydrofuran; hexane | 36% |
cyclohexanespiro-2'-(imidazolidin-4'-thione)-5'-spirocyclohexane
propanoic acid methyl ester
Conditions | Yield |
---|---|
In chloroform-d1 at 20 - 45℃; for 96h; | 99% |
Conditions | Yield |
---|---|
In chloroform-d1 at 20 - 45℃; for 112h; | 99% |
Conditions | Yield |
---|---|
With sodium methylate at 70℃; under 760.051 Torr; for 8h; Temperature; Reagent/catalyst; Large scale; | 98.2% |
Conditions | Yield |
---|---|
cerium (IV) sulfate; silica gel for 1h; Heating; | 98% |
propanoic acid methyl ester
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
triethylene glycol dipropionate
Conditions | Yield |
---|---|
With potassium carbonate at 90 - 95℃; | 98% |
1-(4-methoxy-3-(trifluoromethyl)phenyl)ethanone
propanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 1-[4-Methoxy-3-(trifluoromethyl)phenyl]ethanone With sodium hydride In diethyl ether; mineral oil at 0℃; for 0.5h; Stage #2: propanoic acid methyl ester In diethyl ether; mineral oil at 40℃; for 12h; | 97% |
propanoic acid methyl ester
(RS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine
Conditions | Yield |
---|---|
Stage #1: propanoic acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -80℃; for 0.5h; Stage #2: With triisopropoxytitanium(IV) chloride In tetrahydrofuran; hexane at -80℃; for 0.666667h; Stage #3: (RS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine In tetrahydrofuran; hexane at -80℃; for 3h; diastereoselective reaction; | 96.5% |
propanoic acid methyl ester
(RS,E)-N-ethylidene-2-methylpropane-2-sulfinamide
(RS,2S,3R)-(-)-methyl 3-(N-tert-butanesulfinyl)amino-2-methylbutanoate
Conditions | Yield |
---|---|
Stage #1: propanoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With triisopropoxytitanium(IV) chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #3: (RS,E)-N-ethylidene-2-methylpropane-2-sulfinamide In tetrahydrofuran at -78℃; for 3h; Further stages.; | 96% |
With triisopropoxytitanium(IV) chloride; lithium diisopropyl amide In tetrahydrofuran at -78℃; | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 103℃; Inert atmosphere; Schlenk technique; | 96% |
ethyl oleate
propanoic acid methyl ester
octadec-9-enoic acid methyl ester
Conditions | Yield |
---|---|
titanium(IV) tetraethanolate for 86h; Heating; | 95% |
propanoic acid methyl ester
2-(2-cyclobutanonyl)-6-bromo-3,4-dihydronaphthalene
2-(6-bromo-3,4-dihydronaphthalen-2-yl)-1-(1-(carbmethoxy)ethyl)cyclobutanol
Conditions | Yield |
---|---|
With lithium diisopropyl amide In diethyl ether at -10℃; | 95% |
propanoic acid methyl ester
4-chlorobenzaldehyde
α-Methyl-4-chlorzimtsaeure-methylester
Conditions | Yield |
---|---|
With P(i-BuNCH2CH2)3N at 50℃; for 6h; | 95% |
propanoic acid methyl ester
methyl 3,5-dimethyl-4-[(1'-iodo-2',2'-dimethyl)propyl]pyrrole-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: propanoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: methyl 3,5-dimethyl-4-[(1'-iodo-2',2'-dimethyl)propyl]pyrrole-2-carboxylate With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78 - -55℃; | 95% |
propanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: propanoic acid methyl ester With n-butyllithium; diisopropylamine In diethyl ether; hexane at -80℃; for 0.5h; Stage #2: With triisopropoxytitanium(IV) chloride In diethyl ether; hexane at -80℃; for 0.666667h; Stage #3: (SS)-2-methyl-N-(2,2,2-trifluoroethylidene)-propane-2-sulfinamide In diethyl ether; hexane at -80℃; for 3h; diastereoselective reaction; | 95% |
propanoic acid methyl ester
2-(2-cyclobutanonyl)-6-methoxy-3,4-dihydronaphthalene
2-[1-Hydroxy-2-(6-methoxy-3,4-dihydro-naphthalen-2-yl)-cyclobutyl]-propionic acid methyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide In diethyl ether at -10℃; | 94% |
propanoic acid methyl ester
dimethylaminobis(trifluoromethyl)borane
1-methoxycarbonylethyl-bis(trifluoromethyl)borane-dimethylamine
Conditions | Yield |
---|---|
In pentane dropwise addn. of (CF3)2BNMe2 to a stirred soln. of the carbonyl compound in dry pentane at 4°C; warmed to room temp. with stirring (1 h);; removal of solvent and volatile by-products in vac. at room temp., purifn. by sublimation in vac.; elem. anal.;; | 94% |
propanoic acid methyl ester
[iridium(I)(2,6-bis{(di-tert-butylphosphino)methyl}pyridine)(cyclooctene)](tetrafluoroborate)
Conditions | Yield |
---|---|
at 60℃; for 20h; Inert atmosphere; Schlenk technique; | 94% |
1. | skn-rbt 500 mg/24H MOD | FCTOD7 Food and Chemical Toxicology. 20 (Suppl)(1982),765. | ||
2. | orl-rat LD50:5 g/kg | FCTOD7 Food and Chemical Toxicology. 20 (Suppl)(1982),765. | ||
3. | orl-mus LD50:3460 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 18 (3)(1974),48. | ||
4. | ihl-mus LC50:27 g/m3 | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 18 (3)(1974),48. | ||
5. | orl-rbt LDLo:2550 mg/kg | AMIHAB AMA Archives of Industrial Health. 21 (1960),100. |
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