Triethyl phosphonoacetate → Ethyl 3-(4-fluorophenyl)prop-2-enoate

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Reaction Steps

Sodium hydride (2.11 g, 48.4 mmol) was suspended in anhydrous tetrahydrofuran (60 ml), and diethylphosphonoacetic acid ethyl ester (10.84 g, 48.4 mmol) was added dropwise thereto in an ice bath followed by stirring for 10 minutes. To this mixture solution, a solution of 4-fluorobenzaldehyde (5.00 g, 40.3 mmol) in anhydrous tetrahydrofuran (60 ml) was added dropwise at the same temperature. The reaction solution was stirred for 3 hours, and poured into ice-cold water (150 ml), and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated in vacuo, and then the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=10:1-3:1) to give 4-fluorocinnamic acid ethyl ester (6.69 g, 86% yield) as a colorless oil.

Provenance & Evidence