Pyridine → (R)-2-Hydroxy-2-(6-methoxypyridin-3-yl)ethyl 4-methylbenzenesulfonate

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Reaction Steps

To a stirred solution of (R)-1-(6-methoxypyridin-3-yl)ethane-1,2-diol (2.7 g, 0.016 mol) and pyridine (10 mL) in CH2Cl2 (100 mL) at 0° C. was added p-toluenesulfonyl chloride (3.6 g, 0.019 mol) in small portions. The mixture was slowly warmed to rt and stirred for 24 h, and then diluted with CH2Cl2 (100 mL). The organic phase was washed with aq. NaHCO3, brine, dried (Na2SO4), and concentrated to yield a solid (6.0 g). LC-MS: 324.0 [M+H]+.

Provenance & Evidence