Ethyl 2-chloroacetoacetate → HCID 59594721, compound

HRID 2263377Notes

Reaction equation

HRID 2263377 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.Cl[CH:17]([C:23]([CH3:25])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[CH2:21]([O:20][C:18]([C:17]1[O:12][C:11]([CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)=[N:13][C:23]=1[CH3:25])=[O:19])[CH3:22]

Participants

3

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 53903402HCID 53903402, compound

Product 1

HCID 59594721HCID 59594721, compound

Conditions

Temperature
150 °C

Procedure

18.6 g 3-(4-Trifluoromethyl-phenyl)-propionamide and 42.8 ml ethyl 2-chloroacetoacetate were mixed and stirred at 150° C. for eight hours. Excess ethyl 2-chloroacetoacetate was removed in vacuo (oil pump) and the residue purified by chromatography on silica gel with the eluent petroleum benzene:ethyl acetate=3:1 to obtain 13.75 g 4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole-5-carboxylic acid ethyl ester as an oil.

Workup

  1. customExcess ethyl 2-chloroacetoacetate was removed in vacuo (oil pump)
  2. customthe residue purified by chromatography on silica gel with the eluent petroleum benzene

Sources & evidence

ORD record
ord-2bcc05ae1b1b42b4b9bb3f47d91eab45
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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