Vinyl Acetate → HCID 15232802, compound

HRID 1590343Notes

Reaction equation

HRID 1590343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:19](OC=C)(=[O:21])[CH3:20]>>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1.[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]([O:18][C:19](=[O:21])[CH3:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 15232802HCID 15232802, compound

Product 2

HCID 15232802HCID 15232802, compoundHCID 15232803HCID 15232803, compound

Procedure

The mixture of 5.0 g (20 mmol) of ethyl 3-(3,5-dimethoxyphenyl)-3-hydroxypropionate, 1.4 g (16 mmol) of vinyl acetate and 2.0 g of lipase PS was stirred at room temperature for 8 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 2.2 g (50%ee) of (-)-ethyl 3-(3,5-dimethoxyphenyl)-3-hydroxypropionate and 2.7 g of (+)-ethyl 3-(3,5-di-methoxyphenyl)-3-acetoxypropionate.

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-3dadef9cdd614ce7a3b4d1e8882f58df
Source dataset
uspto-grants-1993_04
Patent number
US05202457

Reaction notes

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