Oxazole → 2-(Tris(propan-2-yl)silyl)-1,3-oxazole

Participants

Reaction Conditions

Reaction Steps

n-BuLi (1.6M in hexanes, 76 mL, 190 mmol) was added dropwise over 30 minutes to a stirred solution of oxazole (12.0 g, 174 mmol) in diethyl ether (400 mL) at −78° C. under argon. The solution was allowed to stir for 60 minutes at −78° C. and then triisopropylsilyl triflate (46.3 mL, 172 mmol) was added dropwise over 30 minutes. The reaction mixture was slowly warmed up to room temperature and stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in hexanes and filtered through a pad of silica gel eluting with 8:1 hexanes/ethyl acetate. Concentration gave the title compound (36.0 g, 93%) as a colourless oil.

Provenance & Evidence