Chlorotrimethylsilane → HCID 67946281, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide was prepared from 2.6 ml of diisopropylamine and 2.8 ml of 1.6M n-butyl lithium in an argon gas stream at -10° C. using anhydrous tetrahydrofuran as a solvent, to which 2.0 g of the compound (C), i.e., 6-methyl-2,6-cyclodecadien-1-one was added dropwise under stirring at -20° C. for 3 min. After stirring the mixture for 15 min, 2.4 ml of trimethyl silyl chloride was added altogether and the temperature was elevated to a room temperature under stirring. The reaction mixture was directly concentrated under a reduced pressure to obtain coarse silyldienol ether. 2.6 g of m-chloroperbenzoic acid was suspended in 100 ml of hexane and stirred at -15° C. for 30 min, to which the above-mentioned coarse product was added and stirred vigorously at -15° to -20° C. for 1.5 hr. After the reaction was completed, the reaction mixture was filtered under suction, and precipitates were washed with hexane and the liquid filtrate and the washing solution were combined and concentrated under a reduced pressure. The resultant oily product was purified on a column chromatography using 50 g of silica gel to obtain 1.4 g (64% yield) of (2Z, 6E)-10-hydroxy-6-methyl-2,6-cyclodecadien-1-one (compound (D)).

Provenance & Evidence