Sodium borohydride → HCID 22650022, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the ketone 6 (1.0 g, 4.0 mmol) in methylene chloride/methanol (3/1 by volume, 40 mL) was added sodium borohydride (1.0 g, 27 mmol). The reaction was monitored by thin layer chromatography (tlc) for the disappearance of the starting ketone, 6. After 1 hr the reaction was worked up diluting with water (30 mL) and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield a yellow solid. The yellow solid as dissolved in benzene (50 mL) containing p-toluenesulfonic acid (10 mg) and heated to 45° C. The reaction mixture was monitored by tlc for the disappearance of the alcohol (45 min). The reaction was worked up by washing with saturated aqueous sodium bicarbonate solution (30 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield 0.66 g (68 percent) of the 8-methylene-1,8-dihydrodibenzo[e,h]azulene, 7, as a yellow oil.

Provenance & Evidence