Hydrochloric Acid → HCID 58604047, compound

Participants

Reaction Conditions

Reaction Steps

2-butyl-5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (263 mg, 0.74 mmol) was dissolved in AcOH (6 mL) then treated with 6N HCl (6 mL). This solution was heated with stirring at 80° C. for 75 minutes, then at 100° C. for 2 hours. After cooling to room temperature the mixture was partitioned between EtOAc/5% NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated under vacuum. Two successive purifications of the crude product by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel columns, eluting with EtOAc/hexane yielded 2-butyl-5-chloro-7-fluoro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one and recovered starting material.

Provenance & Evidence