Benzyl Chloride → (S)-4-benzyloxy-1-trityloxy-2-butanol

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Reaction Steps

Sodium hydride (74 mg, 1.85 mmol, 60% in oil) was loaded under argon circumstance in three necked flask and hexane (2 ml) was added thereto. After stirring for a while, it was allowed to stand and the supernatant was removed by syringe. By repeating this procedure three times, the oil of sodium hydride was removed. After drying in vacuo anhydrous dimethyl sulfoxide (DMSO) (2 ml) was added and the solution was cooled to 0° C. (S)-1-Trityloxy-2,4-butandiol (0.62 g, 1.68 mmol) prepared by Example 2-(2) in DMSO (3 ml) was dropped by taking care of the temperature over a one hour period at room temperature to the solution. Then the solution was stirred for 1 hour. To the solution was dropped benzyl chloride (0.213 ml, 1.85 mol) in DMSO (3 ml) over a one hour period at the range of 0° C. to 5° C. and then the solution was stirred for 4 hours. To the reaction mixture was added water (5 ml) and the solution was extracted with ethyl acetate. The extract was washed with water (8 ml) twice and with saturated brine once, dried on sodium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to (S)-4-benzyloxy-1-trityloxy-2-butanol (0.32 g, yield 45%).

Provenance & Evidence