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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29.6 mg, 0.0847 mmol), 5-benzyl-1-aza-5-stanna-bicyclo[3.3.3]undecane (38.5 mg, 85% weight pure, 0.0935 mmol), and Pd(PPh3)4 (9.8 mg, 0.00848 mmol) in anhydrous toluene (1.3 mL) was degassed, placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 100° C. After heating 4 hours, the cloudy, dark brown reaction mixture was cooled in an ice bath and filtered through a pad of celite. The filtrate was evaporated under vacuum to an orange gum (57 mg). The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, using 9:1 hexanes-EtOAc as developing solvent. The major UV visible band at Rf 0.18-0.26 was removed and eluted with EtOAc to afford 4-benzyl-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg) as a pale yellow gum.

Provenance & Evidence