Methyl 3-acetoxy-2-methylenebutyrate → methyl 2-[(1R)-1-hydroxyethyl]acrylate

HRID 2255657Notes

Reaction equation

HRID 2255657 reaction equation
C([O:4][CH:5]([C:7](=[CH2:12])[C:8]([O:10][CH3:11])=[O:9])[CH3:6])(=O)C>P([O-])([O-])([O-])=O>[OH:4][C@@H:5]([C:7](=[CH2:12])[C:8]([O:10][CH3:11])=[O:9])[CH3:6]

Participants

3

Reactant 1

HCID 5102926Methyl 3-acetoxy-2-methylenebutyrate

Product 1

HCID 11147730methyl 2-[(1R)-1-hydroxyethyl]acrylateYield 17%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A mixture of methyl 2-(1-acetoxyethyl)acrylate (5 g) and "Lipase P" (Trademark; origin : Pseudomonas sp.; maker : Amano Pharmaceutical Co.) (1.25 g) in phosphate buffer solution (0.1M) pH 7.0 (400 ml) was stirred at room temperature for 55 hours. The whole mixture was extracted with ethyl acetate three times and the combined extracts were dried. After removal at 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). The resultant oily residue (840 mg) was distilled in vacuo to give methyl 2-[(1R)-1-hydroxyethyl]acrylate (644 mg).

Workup

  1. extractionThe whole mixture was extracted with ethyl acetate three times
  2. customthe combined extracts were dried
  3. customAfter removal at 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)
  6. distillationThe resultant oily residue (840 mg) was distilled in vacuo

Sources & evidence

ORD record
ord-d60e93df26ee4f8cba1e06dec8077cef
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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