Tetramethyltin → HCID 58604067, 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 (71 mg, 0.15 mmol), dichlorobis(triphenylphosphine)palladium(II) (16 mg, 0.022 mmol), tetramethyltin (0.053 mL, 0.36 mmol), lithium chloride (13 mg, 0.30 mmol), and triphenylphosphine (8 mg, 0.03 mmol) in anhydrous N,N-dimethylformamide (DMF, 0.75 mL) was placed under a N2 atmosphere and heated in an oil bath at 100° C. for 2 days. After cooling, the mixture was concentrated under vacuum, the residue was taken up in CHCl3 and filtered through a pad of silica gel, and the filtrate was evaporated under vacuum to provide an oil. This material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 2:1 hexane-EtOAc. The UV visible band at Rf 0.44-0.50 was eluted with EtOAc and the eluant evaporated under vacuum to provide 6-bromo-3a-butyl-7-(methoxymethoxy)-1-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one contaminated with approximately 10% of 3a-butyl-7-(methoxymethoxy)-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one.

Provenance & Evidence