Chlorotrimethylsilane → Adamantanone

Participants

Reaction Steps

To a solution of 6.6 g 2-methyl-benzoxazol-6-ol (formula IIb) in 100 ml of dry tetrahydrofuran, cooled to 0°, N-ethyldiisopropylamine and trimethylsilyl chloride are added. The mixture is stirred at room temperature for about 2 hours, cooled to −78°, and sodium bis(trimethylsilyl)amide solution is added in portions. To the mixture obtained solid 2-adamantanone (formula VI) is added and the mixture is kept at −78° for about one hour. The reaction mixture is allowed to warm up to room temperature and is pointed into 300 ml of 1 M NaHSO4 solution. The mixture is extracted with ethyl acetate and the organic layer is dried over sodium sulfate. The solvent is evaporated off and the residue is purified by chromatography. The above title compounds are obtained (m.p., respectively, 248-253° and 238-240°).

Provenance & Evidence