Chlorotriethylsilane

• (±)-1-Phenylethyl Alcohol [M0163]
• Chlorotriethylsilane [T0589]
• Imidazole [I0001]
• THF

To a solution of (±)-1-phenylethyl alcohol (0.242 mL, 2.0 mmol) in THF (4 mL, 0.5 mol/L) was added imidazole (204 mg, 3.0 mmol), then TESCl (0.402 mL, 2.4 mmol) was added dropwise and the mixture was stirred at room temperature for 2 hours. Water (10 mL), ethyl acetate (20 mL) was added to the reaction mixture to quench and was extracted with ethyl acetate (10 mL x 3). The combined organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 - 3:97 on silica gel) to give triethyl((±)-1-phenylethoxy)silane as a colorless liquid (373 mg, 79%).

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:20, Rf = 0.70).

triethyl((±)-1-phenylethoxy)silane

¹H NMR (270 MHz, CDCl₃); δ 7.36-7.18 (m, 5H), 4.86 (q, 1H, J = 6.2 Hz), 1.42 (d, 1H, J = 6.2 Hz), 0.94-0.87 (m, 9H), 0.64-0.51 (m, 6H).

• Synthetic Versatility of Lipases: Application for Si-O Bond Formation and Cleavage
• P. B. Brondani, M. Mittersteiner, M. A. Voigt, B. H. Klinkowski, D. R. Scharf, P. C. de Jesus, Synthesis 2019, 51, 477.