Hydrochloric Acid → (2S,4R)-4-p-toluenesulfonyloxy-2-(4-methoxyphenyl)-decanenitrile

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Reaction Steps

To a solution of 559 mg (2.0 mmol) of (2S,4R)-4-hydroxy-2-(4-methoxyphenyl)decanenitrile in 5 ml of pyridine were added, with cooling with ice, a solution of 774 mg (4.1 mmol) of p-toluenesulfonyl chloride (TsCl) in 3 ml of pyridine and 24 mg (0.2 mmol) of 4-(N,N-dimethylamino)pyridine (DMAP). This mixture was stirred at room temperature for 3 days. The pH of the reaction mixture was adjusted to 7 with diluted hydrochloric acid, and this reaction mixture was subjected to extraction with ether (150 ml). The resulting ether solution was washed with diluted hydrochloric acid and saturated sodium chloride aqueous solution, and then concentrated. The residue was separated and purified by column chromatography (Kieselgel 60, hexane/ethyl acetate=4/1), thereby obtaining 550 mg (yield 63%) of (2S,4R)-4-p-toluenesulfonyloxy-2-(4-methoxyphenyl)-decanenitrile.

Provenance & Evidence