Sodium hydride → Methyl 4-(4-(tert-butoxy)-3-(diethoxyphosphoryl)-4-oxobutan-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 2.98 g, 74.7 mmol) was added portionwise to a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (12.6 g, 49.8 mmol) in anhydrous DMF (150 mL) at 23° C. over 20 min. The reaction mixture was cooled to 0° C., and then a solution of methyl 4-(1-bromoethyl)benzoate (12.1 g, 49.8 mmol) in anhydrous DMF (100 mL) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 5 h, then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water (2×). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petrolum ethers to give the title compound. MS: m/z=829.4 (2M+1).

Provenance & Evidence