Pyridinium chloride → 9a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

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Reaction Conditions

Reaction Steps

A mixture of 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (36.6 mg) and pyridine hydrochloride (2.66) was stirred and heated in an oil bath at 190-200° C. for 80 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (20 mL) and water (30 mL). The organic phase was washed with 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 10% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc, the eluant evaporated under vacuum, and the residue lyophilized from benzene to afford 9a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

Provenance & Evidence