Lithium Chloride → HCID 89650431, compound

Participants

Reaction Steps

A solution of benzyl 2-[6,6-dimethyl-2-(trifluoromethylsulfonyloxy)cyclohexen-1-yl]acetate (2.30 g, 5.66 mmol) in dioxane (10 mL) was purged with argon. Then, allyl stannane (2.10 mL, 6.79 mmol), palladium triphenylphosphine tetrakis (327 mg, 0.28 mmol) and lithium chloride (360 mg, 8.49 mmol) were added. The solution was heated to reflux for 7 h and was then concentrated to give a crude yellow oil, which was purified by flash chromatography eluting with cyclohexane and ethyl acetate (25/1) to give the title compound as a colourless oil (1.55 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.33-7.40 (5H, m), 5.72 (1H, ddt, J=16.8, 10.5, 6.2 Hz), 5.11 (2H, s), 4.97 (1H, dt, J=16.8, 1.5 Hz), 4.96 (1H, dt, J=10.5, 1.5 Hz), 3.11 (2H, s), 2.71 (2H, d, J=6.2 Hz), 2.00 (2H, t, J=6.2 Hz), 1.58-1.65 (2H, m), 1.46-1.50 (2H, m), 0.97 (6H, s) ppm.

Provenance & Evidence