Butanoic acid, 3-(acetyloxy)-2-methylene-, ethyl ester → ethyl 2-[(1R)-1-hydroxyethyl]acrylate
Reaction equation
C([O:4][CH:5]([C:7](=[CH2:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:6])(=O)C>P([O-])([O-])([O-])=O>[OH:4][C@@H:5]([C:7](=[CH2:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:6]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 37 °C
Procedure
A mixture of ethyl 2-(1-acetoxyethyl)acrylate (35.65 g) and "Lipase P" (8.88 g) in pH 7.0 phosphate buffer (0.1M) (2.8 l) was stirred at 37° C. for 72 hours. The whole mixture was extracted with ethyl acetate, and the combined extracts were dried. After removal at the solvent from the solution in vacuo, the crude product was purified by column-chromatography on silica gel (eluent : a mixture of hexane and ethyl acetate, 2:1) to give ethyl 2-[(1R)-1-hydroxyethyl]acrylate (11.40 g).
Workup
- extractionThe whole mixture was extracted with ethyl acetate
- customthe combined extracts were dried
- customAfter removal at the solvent from the solution in vacuo
- customthe crude product was purified by column-chromatography on silica gel (eluent
- additiona mixture of hexane and ethyl acetate, 2:1)
Sources & evidence
- ORD record
- ord-0cd7294c2f2d4b569dee246edd633c4c
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05241064
Reaction notes
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