Ammonium Chloride → (E)-[2-(1-hydroxyethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

Participants

Reaction Conditions

Reaction Steps

[step 2] (E)-(2-Formyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (218 mg, 0.84 mmol) obtained in step 1 was dissolved in THF (4 mL), methylmagnesium chloride (3 mol/L THF solution; 0.42 mL, 1.26 mmol) was added at −78° C., and the mixture was warmed to −10° C. over 40 min. Saturated aqueous ammonium chloride solution was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 50/50) to give (E)-[2-(1-hydroxyethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (212 mg, 92%).

Provenance & Evidence