2,2-Dimethoxypropane → (+/-)-4-(Benzyloxymethyl)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane

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Reaction Steps

To a solution of (±)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol (Preparation example 370, 2.4 g, 8.2 mmole) in CH2Cl2 (40 mL) was added p-toluenesulfonyl chloride (15.2 g, 0.08 mmole), and dimethoxypropan (8.4 mL, 9.84 mmole) at 0° C. sequently. The mixture was stirred for 1.5 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (2.2 g, 75˜90%).

Provenance & Evidence