Dibutyltin oxide → HCID 178471345, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1 g (1.86 mmol) of ethyl (7E)-8-{2-[(4-tert-butylbenzyl)oxy]phenyl}-6-[2-(4-cyanophenyl)ethyl]-oct-7-enoate in 70 ml of toluene is mixed with 3.7 ml (27.9 mmol) of trimethylsilyl azide and 694 mg (2.79 mmol) of di-n-butyltin oxide and heated at 80° C. for 12 hours. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). 622 mg (1.1 mmol, 34% of theory) of a white foam are obtained.

Provenance & Evidence