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Substitution (Tosylate)

(Aliphatic Alcohols)


Example 1

To a stirring solution of the alcohol (A) (1.82 g, 8.0 mmol) in DMF (50 mL) was added NaH (0.384 g, 9.6 mmol) portionwise. The mixture was stirred at RT for 30 min, then the tosylate (B) (1.97 g, 8.19 mmol) was added. The reaction mixture was stirred at 55 C for 20 h. The mixture was concentrated, then carefully diluted with H2O, and extracted with EtOAc (3 x 120 mL). The combined organics were washed with H2O, dried (MgSO4), concentrated, and purified by column chromatography (10-20% EtOAc/hexane) to provide the product as a colorless oil. [1.35 g] [WO2014152144, page 52]