Butanoic acid, 3-(acetyloxy)-2-methylene-, ethyl ester → ethyl 2-[(1R)-1-hydroxyethyl]acrylate

HRID 2255658Notes

Reaction equation

HRID 2255658 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

HCID 11063122Butanoic acid, 3-(acetyloxy)-2-methylene-, ethyl ester

Product 1

HCID 10975602ethyl 2-[(1R)-1-hydroxyethyl]acrylateYield 38.5%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A mixture of ethyl 2-(1-acetoxyethyl)acrylate (1 g) and Lipase (0.25 g) in 0.1M phosphate buffer solution (pH 7.0) (80 ml) was stirred at room temperature for 60 hours. The whole mixture was extracted three times with ethyl acetate and the combined extracts were dried over magnesium sulfate. After removal of the solvent 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 (298 mg).

Workup

  1. extractionThe whole mixture was extracted three times with ethyl acetate
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. customAfter removal of the solvent in vacuo
  4. customthe crude product was purified by column chromatography on silica gel (eluent
  5. additiona mixture of hexane and ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-dff8629690a9455aab14e563d877a906
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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