Vinyl Acetate → 6-O-acetylgalactal

HRID 1439989Notes

Reaction equation

HRID 1439989 reaction equation
[O:1]1[C@H:8]([CH2:9][OH:10])[C@H:6]([OH:7])[C@H:4]([OH:5])[CH:3]=[CH:2]1.[C:11](OC=C)(=[O:13])[CH3:12]>O>[C:11]([O:10][CH2:9][C@H:8]1[O:1][CH:2]=[CH:3][C@@H:4]([OH:5])[C@H:6]1[OH:7])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 2734735D-Galactal

Product 1

HCID 143081016-O-acetylgalactal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g (6.85 mmol) of galactal is dissolved in about 1 ml of water, and 1-4 g of crushed molecular sieves, 25-75 ml of vinyl acetate and 800 mg of lipase from Candida cylindracea (Sigma) are added. The mixture is stirred at room temperature for about 45 min. Drying, filtration, concentration in vacuo and chromatography on silica gel (ethyl acetate/hexane 1:1) or crystallization (from ethyl acetate/hexane) yields 1.090 to 1.160 (85-90%) of the desired 6-O-acetylgalactal.

Workup

  1. customDrying
  2. filtrationfiltration, concentration in vacuo and chromatography
  3. customon silica gel (ethyl acetate/hexane 1:1) or crystallization (from ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7d491794963a4560b9e44aef6adadbe0
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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