Chlorotrimethylsilane → HCID 15101118, compound

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Reaction Steps

A solution of ethyl 4-oxocyclohexanecarboxylate (5.95 g) (Example B) in 200 ml of anhydrous tetrahydrofuran is added dropwise under nitrogen to a solution of lithium diisopropylamide (prepared from 4.40 g of diisopropylamine and 26.2 ml of 1.6 M n-butyllithium hexane solution) in 200 ml of tetrahydrofuran at -78° C. The mixture is stirred at this temperature for one hour and trimethylsilyl chloride (4.71 g) is added dropwise via syringe. The reaction mixture is allowed to warm to room temperature overnight and the solvent evaporated in vacuo. The residue is triturated with 100 ml of diethyl ether and filtered to remove inorganic salts. Evaporation of the volatile components of the mixture gives ethyl 4-[(trimethylsilyl)oxy]-3-cyclohexene-1-carboxylate as a colorless oil which is reacted with N-bromosuccinimide and thiourea by following the procedure of Example 1 (Method A) to yield the title compound as a white solid; mp 170°-173° C.

Provenance & Evidence