Dimethylformamide → HCID 86760729, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,6-dibromo-3a-butyl-7-(methoxymethoxy)-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one (139 mg, 0.30 mmol), dichlorobis(triphenylphosphine)palladium(II) (23 mg, 0.03 mmol), lithium chloride (25 mg, 0.60 mmol), triphenylphosphine (16 mg, 0.06 mmol), and anhydrous N,N-dimethylformamide (DMF, 0.6 mL) was purged with N2 and treated with tetramethyltin (0.416 mL, 3.0 mmol). The mixture was stirred under a N2 atmosphere and heated at 100° C. for 22 hours. After cooling, the mixture was concentrated under vacuum, the residue was diluted with EtOAc and filtered through a pad of silica gel, and the filtrate was evaporated under vacuum to provide an oil. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column, eluting with 10:1 hexane-EtOAc (50 mL) followed by 4:1 hexane-EtOAc (100 mL). The product-containing fractions were evaporated under vacuum to afford 3a-butyl-7-(methoxymethoxy-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as an oil.

Provenance & Evidence