Vinyl hexanoate → HCID 12438109, compound

HRID 1590341Notes

Reaction equation

HRID 1590341 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]=[CH:7][C:8]=1[O:9][CH3:10].[C:19](OC=C)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[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]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([O:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 76451Vinyl hexanoateHCID 12438109HCID 12438109, compound

Product 2

HCID 12438109HCID 12438109, compoundHCID 54128437HCID 54128437, compound

Procedure

The mixture of 5.0 g (20 mmol) of ethyl 3-(3,4-dimethoxyphenyl)-3-hydroxypropionate, 1.4 g (13 mmol) of vinyl caproate and 1.0 g of lipase PS was stirred at room temperature for 12 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 g (>50%ee) of (-)-ethyl 3-(3,4-dimethoxyphenyl)-3-hydroxypropionate and 4.3 g (about 43%ee) of (+)-ethyl 3-(3,4-dimethoxyphenyl)-3-hexanoyloxypropionate.

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-a9ca995aa6a54e40b8f10128fb4d67a4
Source dataset
uspto-grants-1993_04
Patent number
US05202457

Reaction notes

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