Potassium Hydroxide → 3-{4-[3-(3,4-Difluoro-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid tert-butyl ester

HRID 556281

Reaction equation

HRID 556281 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=1)=[O:22]>C(O)C.O.O>[C:1]([O:5][C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:20][C:21]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:22])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1230521-(3,4-Difluorophenyl)ethan-1-oneHCID 541476044-Formylcinnamic acid tert-butyl ester

Product 1

HCID 669921713-{4-[3-(3,4-Difluoro-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid tert-butyl esterYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

3-(4-formyl-phenyl)-acrylic acid tert-butyl ester (150 mg, 0.64 mmol) and KOH (72 mg, 1.28 mmol)) were dissolved in ethanol/water (1:1, 5 ml) and 3,4-difluoroacetophenone (83.2 μl, 0.64 mmol) was added to the resulting solution. The resulting mixture was stirred at room temperature overnight and then diluted with H2O. The precipitate was filtered and dried under vacuo to give 210 mg of 3-{4-[3-(3,4-difluoro-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid tert-butyl ester.

Workup

  1. filtrationThe precipitate was filtered
  2. customdried under vacuo

Sources & evidence

ORD record
ord-ecf5a6c5d0f549968aedb114fe1e385a
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Linked notes

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