Diethyl Ether → Trimethyl-(3-methyl-cyclohex-1-enyloxy)-silane

Under nitrogen atmosphere, a suspension of N,N,N′,N′-tetramethylethylenediamine (0.94 mL, 6.24 mmol) and copper iodide (0.42 g, 2.18 mmol) in anhydrous tetrahydrofuran (4 mL) was stirred at room temperature for 5 minutes. The reaction mixture was cooled to −78° C. and a 1.6 M methyl lithium solution in diethyl ether (1.30 mL, 2.08 mmol) was added. After stirring for 20 minutes at the same temperature, trimethylsilyl chloride (0.66 mL, 5.20 mmol) and a solution of cyclohexenone (0.20 g, 2.08 mmol) in anhydrous tetrahydrofuran (2 mL) were added. The reaction mixture was stirred 20 minutes at −78° C. and quenched with a saturated solution of ammonium chloride (10 mL). Diethyl ether (20 mL) was added and the mixture was allowed to reach room temperature. Layers were separated and the organic layer was successively washed with 0.5N hydrochloric acid (15 mL), and a saturated solution of sodium bicarbonate (15 mL), then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to provide trimethyl[(3-methylcyclohex-1-en-1-yl)oxy]silane (17a) (0.20 g, 1.08 mmol, 52%).

1. temperatureThe reaction mixture was cooled to −78° C.
2. stirringThe reaction mixture was stirred 20 minutes at −78° C.
3. customquenched with a saturated solution of ammonium chloride (10 mL)
4. additionDiethyl ether (20 mL) was added
5. customto reach room temperature
6. customLayers were separated
7. washthe organic layer was successively washed with 0.5N hydrochloric acid (15 mL)
8. dry with materiala saturated solution of sodium bicarbonate (15 mL), then dried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography on silica gel (dichloromethane)

ORD record

ord-cba562ac7b824b6a9ba2da9c32d61ac0

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260395B2