Vinyl Acetate → HCID 15232801, compound

HRID 1590342Notes

Reaction equation

HRID 1590342 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:19](OC=C)(=[O:21])[CH3:20]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([O:18][C:19](=[O:21])[CH3:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 19770447HCID 19770447, compound

Product 2

HCID 15232801HCID 15232801, compoundHCID 19770447HCID 19770447, compound

Procedure

The mixture of 5.0 g (20 mmol) of ethyl 3-(2,4-dimethoxyphenyl)-3-hydroxypropionate, 10 ml of vinyl acetate and 2.0 g of lipase PS was stirred at room temperature for 50 days. After the lipase was removed by filtration, the filtrate was eluted by column chromatography (eluting solution; 9/1 of toluene/ethyl acetate) to obtain 3.5 g (35%ee) of (-)-ethyl 3-(2,4-dimethoxyphenyl)-3-hydroxypropionate and 1.5 g of (+)-ethyl 3-(2,4-dimethoxyphenyl)-3-acetoxypropionate, respectively.

Workup

  1. customAfter the lipase was removed by filtration
  2. washthe filtrate was eluted by column chromatography (eluting solution; 9/1 of toluene/ethyl acetate)

Sources & evidence

ORD record
ord-5c60b86ae3ec478498eabd7c8629cedd
Source dataset
uspto-grants-1993_04
Patent number
US05202457

Reaction notes

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