Trityl chloride → (2R)-1-(triphenylmethoxy)-2-propanol

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Dimethylaminopyridine (165 mg, 1.35 mmol) was added to a solution of (R)-propane-1,2-diol (10.3 g, 135.4 mmol) and trityl chloride (38.1 g 136.7 mmol) in DCM (400 mL) at 0° C. Triethylamine (47.2 mL, 338.4 mmol) was then added dropwise to this mixture. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with 1.0 N aq HCl (200 mL), washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give (R)-1-(trityloxy)propan-2-ol (36.4 g, 84%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.43-7.39 (m, 6H) 7.34-7.31 (m, 6H) 7.26-7.22 (m, 3H), 4.70 (d, 1H), 3.82-3.76 (m, 1H), 2.95-2.92 (dd, 1H), 2.70-2.67 (dd, 1H), 1.06 (d, 3H).

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