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

HRID 1439997Notes

Reaction equation

HRID 1439997 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]>C(COC)OC>[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 100476776-O-acetylglucal

Product 1

HCID 143081086-O-acetyl-3-O-chloroacetyl-glucalYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.03 g (5.5 mmol) of 6-O-acetylglucal are taken up in about 2-5 ml of dimethoxyethane and 10 ml of vinyl chloroacetate and stirred with 1 g of lipase P (Amano) at room temperature for about 2-3 h. Filtering off the enzyme, concentration of the solution and chromatography on silica gel (ether/hexane 1:2) result in 6-O-acetyl-3-O-chloroacetyl-glucal in 80-85% yield.

Workup

  1. filtrationFiltering off the enzyme, concentration of the solution and chromatography on silica gel (ether/hexane 1:2)
  2. customresult in 6-O-acetyl-3-O-chloroacetyl-glucal in 80-85% yield

Sources & evidence

ORD record
ord-b649518b4ca342d6a9fac25f62260784
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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