Ammonium tetrafluoride → 4-Cyano-5-methyl-4-(2-naphthyl)hexanol

Participants

Reaction Steps

1.00 g (4.78 mmol) of 3-methyl-2-(2-naphthyl)butyronitrile was dissolved in 20 ml of dimethylformamide, 191 mg (4.78 mmol, 60% by weight) of sodium hydride was added thereto, and the mixture was heated. After 30 minutes; it was cooled to a room temperature, 0.93 ml (4.00 mmol) of (3-bromopropoxy)-tert-butyldimethylsilane was added thereto. After completion of the reaction, brine was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to 50 g of silica gel (ethyl acetate:hexane=1:18), to give 1.40 g of a mixture of the objective product, a raw material and an impurity. The mixture was used for the following reaction without purification. Namely, 1.40 g of the abve-mentioned crude 4-cyano-5-methyl-5-(2-naphthyl)hexanoxy-tert-butyldimethylsilane was dissolved in 20 ml of tetrahydrofuran, and 5 ml (5 mmol) of tetraammonium fluoride was added thereto. After completion of the reaction, brine was added thereto, and the mixture was extracted withethyl acetate. Theorganiclayerwaswashedwith an aqueous saturated ammonium chloride and brine, dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to 50 g of silica gel (ethyl acetate:hexane=1:4), to give 590 mg (2.21 mmol, 46.2%, 2 steps) of the title compound as a yellow oil.

Provenance & Evidence