Sodium hydride → 2-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran

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Reaction Steps

Twenty-two grams of a 55-60% dispersion of sodium hydride in oil are suspended in 200 ml of dry tetrahydrofuran. A solution of 85 g of 3,4-dichlorophenylacetonitrile in 500 ml of tetrahydrofuran is added dropwise at 20° C. over 30 minutes and the reaction mixture is then stirred at room temperature for about two hours. A solution of 98 grams of 2-bromoethoxytetrahydropyran in 100 ml of tetrahydrofuran is added to the reaction mixture cooled to -20° C., the mixture is allowed to warm up to room temperature, and, after two hours, a solution of 50 grams of ammonium chloride in three liters of water is added. Extraction is carried out with 1.5 liters of ethyl ether and the extract is washed with a saturated solution of sodium chloride, decanted, dried over magnesium sulfate, and concentrated under vacuum. The residue is chromatographed on silica gel using dichloromethane as the eluent. The pure product fractions are concentrated to give 3,4-dichloro-α-(2tetrahydropyranyloxyethyl)benzeneacetonitrile as an oil.

Provenance & Evidence