tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]

• 1-Phenylethane-1,2-diol [P0686]
• tert-Butyldimethylchlorosilane [B0995]
• Triethylamine [T0424]
• 4-Dimethylaminopyridine [D1450]
• Dichloromethane

To a solution of 1-phenylethane-1,2-diol (276 mg, 2.0 mmol) in CH₂Cl₂ (4 mL, 0.5 mol/L) was added triethyamine (0.416 mL, 3.0 mmol), TBSCl (362 mg, 2.4 mmol), then DMAP (24.4 mg, 0.20 mmol) was added and the mixture was stirred at room temperature for 1.5 hours. Water (10 mL), CH₂Cl₂ (10 mL) was added to the reaction mixture. The reaction mixture was extracted with CH₂Cl₂ (5 mL x 3) and the 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 = 1:99 - 20 : 80 on silica gel) to give 2-((tert-butyldimethylsilyl)oxy)-1-phenylethan-1-ol as a colorless oil (487 mg, 96%).

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:4, Rf = 0.60).

2-((tert-butyldimethylsilyl)oxy)-1-phenylethan-1-ol

¹H NMR (400 MHz, CDCl₃); δ 7.38-7.26 (m, 5H), 4.80-4.70 (m, 1H), 3.77 (dd, J = 10.3, 3.5 Hz, 1H), 3.56 (dd, J = 10.3, 3.5 Hz, 1H), 2.96 (d, J = 2.2 Hz, 1H), 0.95-0.89 (m, 9H), 0.07-0.05 (m, 6H).

• Enantioselective synthesis of α-hydroxyacids through oxidation of terminal alkenes with AD-mix/TEMPO
• F. J. Aladro, F. M. Guerra, F. J. Moreno-Dorado, J. M. Bustamante, Z. D. Jorge, G. M. Massanet, Tetrahedron Lett. 2000, 41, 3209.