Sodium hydride → HCID 73804349, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% in mineral oil, 3.11 g, 77.86 mmol) is suspended in dry tetrahydrofuran (160 mL) and cooled to 0° C. Trimethylphosphonoacetate (14.18 g, 77.86 mmol) is added and the mixture stirred at 0° C. for 30 minutes. 2-Fluoro-4-methoxybenzaldehyde (10 g, 64.88 mmol) is added and the mixture stirred overnight at room temperature. (Carbethoxymethylene)triphenylphosphorane (11.3 g, 32.44 mmol) is added and the mixture stirred for 3 hours. Saturated aqueous ammonium chloride solution is added and the mixture extracted with ethyl acetate. The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (5% ethyl acetate in cyclohexane) to give the title compound (yield 13.85 g).

Provenance & Evidence