Water → 1-(Hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

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Reaction Steps

560 mg of ethyl 5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxylate prepared in Example 1-b was dissolved in 20 ml dry tetrahydrofuran, and 120 mg of lithium aluminum hydride was added under ice-cooling, followed by stirring for 2 hours. To the reaction mixture were successively added 0.1 ml of water, 0.1 ml of 15% potassium hydroxide solution and 0.3 ml of water, followed by stirring at room temperature for 0.5 hour. The reaction mixture was filtered through Celite, washed with ethyl acetate, and the solvent was evaporated, to give 500 mg of the title compound as a colorless oil.

Provenance & Evidence