Stannane, tributyl(1-ethoxyethenyl)- → HCID 22491033, compound

Participants

Reaction Steps

To a solution of mixture B (2.18 g, 7.21 mmol) in THF (40 mL) was added tributyl(1-ethoxyvinyl)tin (3.66 mL, 10.8 mmol). After the mixture was degassed via bubbling argon for 30 min, dichlorobis(triphenylphosphine)palladium (II) (0.25 g, 0.05 mmol) was added. The reaction mixture was heated to reflux for 48 h. Because the reaction was incomplete via TLC, another 0.5 eq tributyl(1-ethoxyvinyl)tin and 0.05 eq dichlorobis(triphenylphosphine)palladium (II) were added and the mixture was heated at reflux for overnight. The reaction mixture was cooled to room temperature and quenched with water and 10% HCl. After stirring at room temperature for 30 min, the mixture was extracted with ether. The combined ethereal layers were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 1% ethyl acetate in hexanes) gave a separable mixture of 1-(3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-24) and the title compound.

Provenance & Evidence