Vinyl Acetate → 3-O-acetyl-6-O-benzoylgalactal

HRID 1439996Notes

Reaction equation

HRID 1439996 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.[C:19](OC=C)(=[O:21])[CH3:20]>C(COC)OC>[C:19]([O:17][C@H:13]1[C@@H:12]([OH:18])[C@@H:11]([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:16][CH:15]=[CH:14]1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 143081066-O-benzoylgalactal

Product 1

HCID 143081153-O-acetyl-6-O-benzoylgalactalYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.0 g (4 mmol) of 6-O-benzoylgalactal is taken up in 10-15 ml of dimethoxyethane (DME) and 20-25 ml of vinyl acetate and stirred with 1 g of lipase P at room temperature for 8 h, Filtering off the enzyme and crystallization or chromatography on silica gel (ether/hexane 1:1) yield 3-O-acetyl-6-O-benzoylgalactal in 80-85% yield,

Workup

  1. filtrationFiltering off
  2. customthe enzyme and crystallization or chromatography on silica gel (ether/hexane 1:1)

Sources & evidence

ORD record
ord-5808e22be8b344b08d83a00b923e26a6
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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