Vinyl hexanoate → Methyl 3-hydroxy-3-phenylpropanoate

HRID 1590340Notes

Reaction equation

HRID 1590340 reaction equation
[C:1]1([CH:7]([OH:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](OC=C)(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[C:1]1([CH:7]([OH:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH:7]([O:13][C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 76451Vinyl hexanoateHCID 347841Methyl 3-hydroxy-3-phenylpropanoate

Product 2

HCID 347841Methyl 3-hydroxy-3-phenylpropanoateHCID 15232799(+)-Methyl 3-phenyl-3-hexanoyloxy-propionate

Procedure

The mixture of 5.0 g (28 mmol) of methyl 3-phenyl-3-hydroxypropionate, 1.97 g (14 mmol) of vinyl caproate and 2.0 g of lipase PS was stirred at room temperature for 28 hours. After the lipase was removed by filtration, the filtrate was eluted by column chromatography (eluting solution; 9/1 of toluene/ethyl acetate). 2.35 g (88%ee) of (-)-methyl 3-phenyl-3-hydroxypropionate and 3.97 g (91%ee) of (+)-methyl 3-phenyl-3-hexanoyloxy-propionate were obtained, 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-9e15632f6d544ceb84d67d8ac57835dd
Source dataset
uspto-grants-1993_04
Patent number
US05202457

Reaction notes

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