Water → HCID 86751396, compound

HRID 1489451Notes

Reaction equation

HRID 1489451 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@@H:16]([OH:33])[C@H:17](OS(C1C=CC(C)=CC=1)(=O)=O)[C:18]([O:20][CH3:21])=[O:19].C(OCC)(=O)C>CN(C)C=O>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C@H:16]1[O:33][C@H:17]1[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 54390514HCID 54390514, compound

Product 1

HCID 86751396HCID 86751396, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.26 ml of water and 1.20 g of potassium carbonate were added to a solution of 1.12 g of methyl (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-(p-toluenesulfonyloxy)propionate dissolved in 15 ml of dimethylformamide, and the mixture was stirred at room temperature overnight. Ethyl acetate and ice water were added to the reaction mixture, and the organic layer was collected by separation. After the organic layer was washed with water and dried, the solvent was removed. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1) to obtain 502 mg of methyl (2R,3R)-3-(2,4-difluorophenyl)-2-epoxypropionate.

Workup

  1. customthe organic layer was collected by separation
  2. washAfter the organic layer was washed with water
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-cb5e68c1417b4bc0bd287ee9dc10bf95
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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