4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one → 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.138 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.276 mL) was treated with copper(I) cyanide (25 mg, 0.275 mmol). The resulting mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 160° C. for 40 minutes. The mixture was partitioned between EtOAc (20 mL) and water (20 ml). The organic phase was washed with water (2×20 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg) as an oil.

Provenance & Evidence