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Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 9h; Baylis-Hillman reaction; | 90% |
With 1,4-diaza-bicyclo[2.2.2]octane In methanol at 20℃; for 9h; Baylis-Hillman reaction; | 90% |
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 12h; | 90% |
formaldehyd
(methyloxycarbonylmethyl)triphenylphosphonium bromide
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With potassium carbonate In water at 10 - 20℃; for 6h; | 85% |
1,4-diaza-bicyclo[2.2.2]octane
acrylic acid methyl ester
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With formaldehyd; paraformaldehyde In diethyl ether; nitrogen | 77% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd With phosphoric acid In water at 90℃; for 5h; Stage #2: trimethyl phosphonoacetate With potassium carbonate In water at 35 - 40℃; for 0.9h; | 62% |
With potassium carbonate In water at 20℃; for 1h; | 55% |
With potassium carbonate In water at 20℃; for 2h; | 44% |
With potassium carbonate at 30 - 35℃; for 1h; |
formaldehyd
acrylic acid methyl ester
A
methyl 2-hydroxymethylacrylate
B
dimethyl 2,2′-[oxybis(methylene)]diacrylate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 95℃; for 4h; | A 23% B 60% |
formaldehyd
trimethyl phosphonoacetate
A
methyl 2-hydroxymethylacrylate
B
acrylic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In water at 23℃; | A 56% B n/a |
1,4-diaza-bicyclo[2.2.2]octane
acrylic acid methyl ester
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
In cyclohexanol | 45% |
formaldehyd
ethyl acrylate
A
methyl 2-hydroxymethylacrylate
B
dimethyl 2,2′-[oxybis(methylene)]diacrylate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane for 19h; Heating; | A n/a B 13% |
2-acetoxymethyl-acrylic acid
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With methanol; sulfuric acid |
methanol
propargyl alcohol
tetracarbonyl nickel
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
(i) AcOH, (ii) /BRN= 506003/, (iii) H2SO4; Multistep reaction; |
methanol
ethyl 2-(hydroxymethyl)acrylate
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With potassium carbonate at 20℃; for 4h; |
methanol
carbon monoxide
propargyl alcohol
A
methyl 2-hydroxymethylacrylate
B
methyl α-methoxymethylacrylate
Conditions | Yield |
---|---|
With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine In 1,2-dichloro-ethane at 50℃; under 22801.5 Torr; for 3h; Catalytic behavior; Inert atmosphere; Schlenk technique; Autoclave; regioselective reaction; | A 23.8 %Chromat. B 71.4 %Chromat. |
Conditions | Yield |
---|---|
With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine In 1,2-dichloro-ethane at 50℃; under 22801.5 Torr; for 3h; Catalytic behavior; Temperature; Pressure; Solvent; Inert atmosphere; Schlenk technique; Autoclave; regioselective reaction; | 95.2 %Chromat. |
methanol
propargyl alcohol
A
methyl 4-hydroxy-2-butenoate
B
methyl 2-hydroxymethylacrylate
C
methyl α-methoxymethylacrylate
Conditions | Yield |
---|---|
With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine In 1,2-dichloro-ethane at 60℃; under 22801.5 Torr; for 20h; Catalytic behavior; Inert atmosphere; Schlenk technique; Autoclave; regioselective reaction; | A 6.1 %Chromat. B 21.6 %Chromat. C 72.2 %Chromat. |
With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine In 1,2-dichloro-ethane at 60℃; under 22801.5 Torr; for 3h; Catalytic behavior; Inert atmosphere; Schlenk technique; Autoclave; regioselective reaction; | A 5.9 %Chromat. B 85.6 %Chromat. C 8.5 %Chromat. |
methanol
propargyl alcohol
A
methyl 4-hydroxy-2-butenoate
B
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With methanesulfonic acid; palladium diacetate; diphenyl-(6-methyl-pyridin-2-yl)phosphine In 1,2-dichloro-ethane at 50℃; under 22801.5 Torr; for 3h; Catalytic behavior; Inert atmosphere; Schlenk technique; Autoclave; regioselective reaction; | A 5.3 %Chromat. B 94.7 %Chromat. |
methyl 2-hydroxymethylacrylate
acetyl chloride
methyl 2-(1-acetoxymethyl)acrylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Schlenk technique; Inert atmosphere; | 100% |
With pyridine In dichloromethane at -12 - 20℃; for 3h; Inert atmosphere; | 85% |
With triethylamine In dichloromethane at 0 - 20℃; | 71% |
With pyridine In diethyl ether at 20℃; for 0.5h; Inert atmosphere; | 44% |
With pyridine In dichloromethane at 0 - 20℃; for 24h; |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane | 100% |
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With Co(dmgBF2)2(THF)2; hydrogen In benzene at 50℃; for 24h; | 100% |
methyl 2-hydroxymethylacrylate
methyl 3-hydroxy-2-methylpropanoate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; | 97% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; N(1)-(4-butylphenyl)-N(2)-(4-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)phenyl)phthalamide; hydrogen In dichloromethane at 20℃; under 37503.8 Torr; for 20h; Autoclave; | |
With bis(norbornadiene)rhodium(l)tetrafluoroborate; C50H44N3O2P; C112H112N8O8Zn; hydrogen In dichloromethane at 25℃; under 7500.75 Torr; for 16h; | |
With bis(norbornadiene)rhodium(l)tetrafluoroborate; C6H15N*C27H29F3NO4PSSi2; C27H26NO4P; hydrogen In dichloromethane under 15001.5 Torr; for 18h; Reagent/catalyst; enantioselective reaction; | n/a |
With palladium 10% on activated carbon; hydrogen; potassium carbonate In methanol at 20℃; under 760.051 Torr; for 7h; |
methyl 2-hydroxymethylacrylate
tert-butylchlorodiphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 20℃; for 1h; | 97% |
In N,N-dimethyl-formamide at 0 - 20℃; for 19h; | 89% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 16h; | 87% |
(5-methyl-pyridin-2-yl)amine
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux; | 95% |
With N-heterocyclic carbene palladium(II) complex supported on fibrous nanosilica In trifluoroacetic acid for 1h; Reflux; Green chemistry; chemoselective reaction; |
methyl 2-hydroxymethylacrylate
acryloyl chloride
Conditions | Yield |
---|---|
With triethylamine | 92% |
chloro-trimethyl-silane
methyl 2-hydroxymethylacrylate
methyl 2-trimethylsilyloxymethylacrylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 92% |
3-methylpyridin-2-ylamine
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux; | 92% |
With N-heterocyclic carbene palladium(II) complex supported on fibrous nanosilica In trifluoroacetic acid for 1h; Reflux; Green chemistry; chemoselective reaction; |
methyl 2-hydroxymethylacrylate
tert-butyldimethylsilyl chloride
2-(tert-butyl-dimethyl-silanyloxymethyl)-acrylic acid methyl ester
Conditions | Yield |
---|---|
With dmap; TEA In dichloromethane at 0 - 20℃; | 91% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; Inert atmosphere; | 82% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; Sealed tube; Inert atmosphere; | 81% |
methyl 2-hydroxymethylacrylate
benzylamine
methyl 2-[(N-benzylamino)methyl]-3-hydroxypropanoate
Conditions | Yield |
---|---|
In methanol at 20℃; for 16h; | 91% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; | 91% |
2-aminopyridine
methyl 2-hydroxymethylacrylate
3-methyl-2H-pyrido[1,2-a]pyrimidin-2-one
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol for 12h; Reflux; | 90% |
With N-heterocyclic carbene palladium(II) complex supported on fibrous nanosilica In trifluoroacetic acid for 1h; Solvent; Reagent/catalyst; Reflux; Green chemistry; chemoselective reaction; |
methyl 2-hydroxymethylacrylate
methyl 2-(bromomethyl)propenoate
Conditions | Yield |
---|---|
With phosphorus tribromide In diethyl ether Inert atmosphere; | 89% |
With phosphorus tribromide In diethyl ether at 0 - 20℃; for 2h; | 87.4% |
With phosphorus tribromide In acetonitrile at 20℃; for 4h; | 86% |
dimethylsulfide
methyl 2-hydroxymethylacrylate
methyl 2-(bromomethyl)propenoate
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sodium chloride In diethyl ether; dichloromethane | 89% |
methyl 2-hydroxymethylacrylate
N-benzyloxy-α-methyl-α-bromopropionamide
Conditions | Yield |
---|---|
With sodium carbonate at 20℃; for 3h; Inert atmosphere; | 89% |
methyl 2-hydroxymethylacrylate
3-hydroxy-(2S)-methylpropionate
Conditions | Yield |
---|---|
With diisopropyl{1-[(S)-3,5-dioxa-4-phospha-cyclohepta(2,1-a;3,4-a')dinaphthalen-4-yl]-3-methyl-2-indolyl}phosphine; bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen In dichloromethane at -40℃; under 15001.5 Torr; for 15h; Reactivity; Pressure; Temperature; Concentration; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 87% |
With N-methyl-N-{(S)-1-[2-(diphenylphosphino)phenyl]ethyl}-(S)-1,10-bi-2-naphthylphosphoramidite; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen In dichloromethane at 20℃; under 7500.75 Torr; for 24h; optical yield given as %ee; | |
With BF4(1-)*C8H10Rh(1+)*C17H27NO2P2; hydrogen In dichloromethane at 25℃; under 750.075 Torr; for 1.5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.216667h; Mitsunobu Displacement; Inert atmosphere; Schlenk technique; stereoselective reaction; | 87% |
methyl 2-hydroxymethylacrylate
2-(hydroxymethyl)acrylic acid
Conditions | Yield |
---|---|
With methanol; potassium hydroxide In tetrahydrofuran; water at 20℃; for 24h; | 85% |
triisopropylsilyl chloride
methyl 2-hydroxymethylacrylate
methyl 2-(((triisopropylsilyl)oxy)methyl)acrylate
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 20℃; for 1h; | 85% |
With 1H-imidazole; dmap In dichloromethane at 20℃; for 18h; Inert atmosphere; | 123.3 mg |
With 1H-imidazole In dichloromethane Inert atmosphere; |
2-amino-5-iodopyridine
methyl 2-hydroxymethylacrylate
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux; | 85% |
With N-heterocyclic carbene palladium(II) complex supported on fibrous nanosilica In trifluoroacetic acid for 1h; Reflux; Green chemistry; chemoselective reaction; |
methyl 2-hydroxymethylacrylate
2-chloro-1,1,1-trimethoxyethane
Conditions | Yield |
---|---|
With acetic acid In toluene at 130℃; for 24h; | 85% |
methyl 2-hydroxymethylacrylate
Cinnamyl bromide
Conditions | Yield |
---|---|
Stage #1: methyl 2-hydroxymethylacrylate With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique; Stage #2: Cinnamyl bromide In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; | 84% |
methyl 2-hydroxymethylacrylate
3-fluoropyridin-2-amine
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux; | 83% |
methyl 2-hydroxymethylacrylate
3-bromo-5-methylpyridin-2-amine
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux; | 83% |
cyclopentadienyl titanium(IV) trichloride
methyl 2-hydroxymethylacrylate
(2-carbethoxyprop-2-enoxy)bischloro-η5-cyclopentadienyl titanium(IV)
Conditions | Yield |
---|---|
With triethylamine In benzene (Ar); stirring (2 h); evapn. (vac.), sublimation (80°C, 0.01 Torr), recrystn. (toluene/hexanes); elem. anal.; | 82% |
methyl 2-hydroxymethylacrylate
4-nitro-benzoyl chloride
4-nitrobenzoic acid 2-methoxycarbonyl-allyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 0.75h; | 81% |
methyl 2-hydroxymethylacrylate
(E)-3,5-hexadienoic acid
(E)-Hexa-3,5-dienoic acid 2-methoxycarbonyl-allyl ester
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide In diethyl ether at 0℃; for 12h; | 78% |
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