Chlorotrimethylsilane → HCID 53911366, compound

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.

1. additionOnce the addition
2. additionmethyl β-cyclogeranate (20.0 g, 109.8 mmol) was added to the resulting blue-grey solution at 35°-40°
3. temperaturecooled to -30°
4. customThe cooling bath was removed
5. stirringstirring
6. waitwas kept for 2 h at 20°
7. additionThe yellow mixture was treated with a saturated solution of NaHCO3 /ice/petroleum ether
8. extractionextracted
9. washThe organic layer was washed with water and saturated NaCl
10. dry with materialdried over Na2SO4
11. customevaporated
12. distillationdistilled (55°-60°/6.7 Pa)

ORD record

ord-fb2d5f1f51434f0ab030e2770f4caee7

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05114915