Vinyl chloroacetate → 6-O-benzoyl-3-O-chloroacetyl-galactal

HRID 1440000Notes

Reaction equation

HRID 1440000 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:16][CH:15]=[CH:14][C@@H:13]([OH:17])[C@H:12]1[OH:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][C:21](OC=C)=[O:22]>COCCOC>[C:1]([O:9][CH2:10][C@H:11]1[O:16][CH:15]=[CH:14][C@@H:13]([O:17][C:21](=[O:22])[CH2:20][Cl:19])[C@H:12]1[OH:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82156Vinyl chloroacetateHCID 143081066-O-benzoylgalactal

Product 1

HCID 143081126-O-benzoyl-3-O-chloroacetyl-galactalYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.0 g (4 mmol) of 6-O-benzoylgalactal is taken up in about 20-25 ml of DME and 10-15 ml of vinyl chloroacetate and stirred with 1 g of lipase from Pseudomonas spec. (lipase P, Amano) at room temperature for about 5-7 h. Filtering off the reusable enzyme, concentration of the solution in vacuo and chromatography on silica gel (ether/hexane 1:1) or crystallization result in 6-O-benzoyl-3-O-chloroacetyl-galactal in 80% yield (1050 mg).

Workup

  1. filtrationFiltering off the reusable enzyme, concentration of the solution in vacuo and chromatography
  2. customon silica gel (ether/hexane 1:1) or crystallization
  3. customresult in 6-O-benzoyl-3-O-chloroacetyl-galactal in 80% yield (1050 mg)

Sources & evidence

ORD record
ord-41fa0452cb4b4029a8f77fe6131899dd
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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