Vinyl hexanoate → HCID 12566301, compound

HRID 1590344Notes

Reaction equation

HRID 1590344 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:16](OC=C)(=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 76451Vinyl hexanoateHCID 12566301HCID 12566301, compound

Product 2

HCID 12566301HCID 12566301, compoundHCID 53934674HCID 53934674, compound

Procedure

The mixture of 5.0 g of ethyl 3-(3-chlorophenyl)-3-hydroxypropionate, 1.6 g of vinyl caproate and 2.0 g of lipase PS was stirred at room temperature for 13 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 2.34 g (40%ee) of (-)-ethyl 3-(3-chlorophenyl)-3-hydroxypropionate and 2.75 g (>90%ee) of (+)-ethyl 3-(3-chlorophenyl)-3-caproyloxypropionate.

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-5a4b86643f2443418adaefe533d06b59
Source dataset
uspto-grants-1993_04
Patent number
US05202457

Reaction notes

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