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

HRID 1439998Notes

Reaction equation

HRID 1439998 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:11][CH:10]=[CH:9][C@@H:8]([OH:12])[C@H:7]1[OH:13])(=[O:3])[CH3:2].[Cl:14][CH2:15][C:16](OC=C)=[O:17]>COCCOC>[C:1]([O:4][CH2:5][C@H:6]1[O:11][CH:10]=[CH:9][C@@H:8]([O:12][C:16](=[O:17])[CH2:15][Cl:14])[C@H:7]1[OH:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 82156Vinyl chloroacetateHCID 143081016-O-acetylgalactal

Product 1

HCID 143081096-O-acetyl-3-O-chloroacetyl-galactalYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.03 g (5.5 mmol) of 6-O-acetylgalactal are taken up in 10-15 ml of DME and 20-25 ml of vinyl chloroacetate and stirred with 1 g of lipase P (Pseudomonas spec.) at room temperature for 5-6 h. Filtering off the reusable enzyme, concentration of the solution and chromatography (SiO2, ether/hexane 1:2) result in 6-O-acetyl-3-O-chloroacetylgalactal in 80% yield.

Workup

  1. filtrationFiltering off the reusable enzyme, concentration of the solution and chromatography (SiO2, ether/hexane 1:2)
  2. customresult in 6-O-acetyl-3-O-chloroacetylgalactal in 80% yield

Sources & evidence

ORD record
ord-8ab161a4355f488d918636f195048e2c
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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