Sodium hydride → HCID 89120268, compound

Participants

Reaction Steps

To a suspension of 1.71 g sodium hydride (50% in oil, 35.7 mmol) in anhydrous tetrahydrofuran (100 mL) was added a solution of 8.0 g tert-butyl P,P-dimethylphosphonoacetate (35.7 mmol) in anhydrous tetrahydrofuran (25 mL) at room temperature, and the resulting mixture was stirred for 1 h at room temperature. Subsequently, a solution of 4.95 g 4-benzyloxybenzyl bromide (17.8 mmol; prepared according to Helv. Chim. Acta, 2002, 85, 3422) in tetrahydrofuran (25 mL) was added, and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride (50 mL) was then added, the mixture was stirred for another 20 minutes at room temperature, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. Column chromatography over silica gel (2.5→50% ethyl acetate in hexane) gave 1.48 g (20% yield based on 4-benzyloxybenzyl bromide) of the target compound.

Provenance & Evidence