Sodium hydride → 3-[2-Iodo-5-(trifluoromethyl)benzyl]-6-phenyl-1,3-oxazinan-2-one

Participants

Reaction Steps

A stirred and cooled (0° C.) suspension of sodium hydride (60% suspension in mineral oil, 14 mg, 0.34 mmol) in THF (2 mL) was treated dropwise with a solution of 6-phenyl-1,3-oxazinan-2-one (24 mg, 0.137 mmol) in THF (2 mL), under an atmosphere of nitrogen. The reaction was stirred for 20 min at 0° C. and 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene (Intermediate 11; 50 mg, 0.137 mmol) was added. The reaction was allowed to warm to room temperature and stirred for an additional 3 h. Saturated NH4Cl (1 mL) was added and the resultant mixture was partitioned between H2O (20 mL) and EtOAC (20 mL). The aqueous layer was re-extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine (40 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 3-[2-iodo-5-(trifluoromethyl)benzyl]-6-phenyl-1,3-oxazinan-2-one as a colorless oil. LCMS=462.0 (M+1)+.

Provenance & Evidence