Chlorotrimethylsilane → HCID 53911366, compound

Participants

Reaction Steps

A solution of butyllithium in hexane (118 ml, 1.40N, 164.8 mmol) was added at a temperature of between -10° and 0° to a stirred solution of diisopropylamine (17.20 g, 24.3 ml, 170.0 mmol) in THF (120 ml). Once the addition was completed, the yellow solution was treated with an allylmagnesium chloride solution in THF (119.0 ml, 1.38N, 164.6 mmol) at 20°, and methyl β-cyclogeranate (20.0 g, 109.8 mmol) was added to the resulting blue-grey solution at 35°-40°. The resulting yellow mixture was stirred at the same temperature for 1 h, cooled to -30° and treated with (C2H5)3N (22.2 g, 30.4 ml, 219.6 mmol) and (CH3)3SiCl (35.6 g, 41.4 ml, 329.4 mmol). The cooling bath was removed and stirring was kept for 2 h at 20°. The yellow mixture was treated with a saturated solution of NaHCO3 /ice/petroleum ether and extracted. The organic layer was washed with water and saturated NaCl, dried over Na2SO4, evaporated and distilled (55°-60°/6.7 Pa). 24.4 G of 1,3,3-trimethyl-2-[1-(trimethylsilyloxy)-1,3-butadienyl]-1-cyclohexene were obtained, in the form of an E/Z=3:1 isomer mixture (95% pure, 80% yield). IR: 2920, 1620, 1580, 1455, 1245, 1205, 1160, 1060 cm-1.

Provenance & Evidence