Sodium hydride → HCID 15614943, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% by weight dispersion in mineral oil 0.208 g, 1.1 eq) was added to a stirred solution of N-[[2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, ethyl ester (2.26 g, 6.29 mmol) in anhydrous tetrahydrofuran (75 mL) at room temperature under a dry nitrogen atmosphere. After 45 minutes, the t-butyl bromoacetate (1.52 mL, 1.5 eq) was added and the reaction was heated to 60° C. After 11/4 hours of heating, the reaction was cooled to room temperature and the THF was removed. The residue was suspended in ether (150 mL), washed with water (2×75 mL) and saturated aqueous NaCl (1×50 mL), dried with MgSO4, and the ether was removed. The crude oil was flash chromatographed (4:1 petroleum ether:ethyl acetate, silica) then triturated with petroleum ether (3×30 mL) to provide the title compound as a white powder (2.40 g, 81%), m.p. 81°-83° C.

Provenance & Evidence