Ammonium Chloride → (3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane

Temperature

65 °C

To a solution of trimethylsilyl acetylene (851 μL, 6.02 mmol) in tetrahydrofuran (20 mL) was added ethyl magnesium bromide (3 M diethyl ether solution, 1.86 mL, 5.59 mmol) under nitrogen atmosphere at room temperature, which was stirred for 40 minutes at 65° C. The reaction solution was cooled to room temperature, and copper (I) bromide (308 mg, 2.16 mmol) and 4-benzyloxybenzyl chloride (1.00 g, 4.30 mmol) were added to the reaction solution and stirred for 8 hours and 45 minutes at 65° C. Saturated ammonium chloride solution was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (911 mg, 72%).

1. temperatureThe reaction solution was cooled to room temperature
2. stirringstirred for 8 hours and 45 minutes at 65° C
3. extractionwhich was then extracted with ethyl acetate
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under a reduced pressure
7. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1)

ORD record

ord-7cec689e16cf43e5950b9715356415a2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2