1,3-Diethyl 2-oxopropanedioate → Diethyl 2-[2-(2,3-difluorophenyl)-2-oxoethyl]-2-hydroxymalonate

HRID 2214747Notes

Reaction equation

HRID 2214747 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[O:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH2:10][C:13]([OH:12])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 5195502',3'-Difluoroacetophenone

Product 1

HCID 21948264Diethyl 2-[2-(2,3-difluorophenyl)-2-oxoethyl]-2-hydroxymalonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2′,3′-Difluoroacetophenone (10.23 g, 65.6 mmol) and diethyl ketomalonate (15 mL, 98.4 mmol) were stirred at 140° C. for 48 hours. The crude mixture was diluted with toluene and purified by chromatography on silica gel, eluting with 20% v/v ethyl acetate in hexane to afford the title compound as an oil.

Workup

  1. custompurified by chromatography on silica gel
  2. washeluting with 20% v/v ethyl acetate in hexane

Sources & evidence

ORD record
ord-16b780f05db145f48b735c808e0d3a7e
Source dataset
uspto-grants-2006_09
Patent number
US07109199B2

Reaction notes

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