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

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Reaction Steps

20 g of sodium hydride as a 55-60% dispersion in oil are suspended in 200 ml of dry tetrahydrofuran. A solution of 85 g of 3,4-dichlorophenylacetonitrile in 500 ml of THF is added dropwise at 20° C. in 30 minutes and the reaction mixture is then stirred at RT for 2 hours. It is cooled to -20° C., a solution of 98 g of 2-(2-bromoethoxy)tetrahydropyran in 100 ml of THF is added, the mixture is allowed to return to RT and, after 2 hours, a solution of 50 g of ammonium chloride in 3 liters of water is added. Extraction is carried out with 1.5 liters of ether and the extract is washed with saturated sodium chloride solution, decanted, dried over MgSO4 and concentrated under vacuum.

Provenance & Evidence