Diisopropyl Ether → 2,2-Dimethyl-8-phenoxy-4-(1H-1,2,4-triazol-1-yl)octan-3-one

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Reaction Steps

A solution of 14.3 g of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one (cf. German Laid-Open Application DOS No. 2,638,470) in 20 ml of DMF is added dropwise, under a dry nitrogen atmosphere, to a stirred suspension of 2.3 g of sodium hydride in 20 ml of dimethylformamide (DMF), the reaction temperature being kept at 20°-30° C. by cooling; the mixture is subsequently stirred for 20 hours at room temperature. A solution of 19.5 g of 1-bromo-4-phenoxybutane in 20 ml of DMF is then added dropwise at 5°-10° C., with continued stirring, and whilst cooling with ice. After completion of the addition, stirring is continued for 10 hours at 5°-10° C., after which 200 ml of water are added and the mixture is extracted twice with 100 ml of methylene chloride at a time. The combined organic phases are extracted by shaking with water and dried over magnesium sulfate; removal of the solvent under reduced pressure gives an oil from which, on trituration with 20 ml of diisopropyl ether, 17 g of colorless crystals precipitate; melting point 59°-62° C.

Provenance & Evidence