Water → 2-Trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin

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Reaction Steps

To the mixture of 0.2g of lithium aluminum hydride and 20ml of anhydrous tetrahydrofuran was added with stirring under ice-cooling 400mg of 2-trifluoromethyl-9-chloro-11-chloro-10,11-dihydrodibenzo[b,f]thiepin dissolved in 10ml of anhydrous tetrahydrofuran. Thereafter, the mixture was reacted under cooling for 0.5 hr. at the room temperature and further under reflux condition for 3.5 hrs. After cooling, to the mixture was added water with stirring under cooling to decompose an excess of lithium aluminum hydroxide and the resulting mixture was filtered with the use of celite. The filtrate was extracted with chloroform, chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 372ml of an oily substance, which was chromatographed on a silica gel, eluted with n-hexane, and there was obtained 65mg of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin.

Provenance & Evidence