Benzyl Alcohol → HCID 131735655, compound

Participants

Reaction Steps

Ethyl 4-cyclopropyl(dimethyl)silyl-3-cyanobutanoate (6.39 g, 26.7 mmol) obtained in Example 3 mentioned above was hydrolyzed by using lithium hydroxide in the same manner as that of the aforementioned examples. The obtained reaction mixture (6.21 g) was dissolved in dichloromethane (85 ml), and the solution was added successively with benzyl alcohol (4.95 ml, 48.1 mmol), dicyclohexylcarbodiimide (8.81 g, 42.8 mmol) and 4-dimethylaminopyridine (163 mg, 1.34 mmol). The mixture was stirred for 30 minutes under ice cooling and for further 17 hours at room temperature. After the reaction vessel was cooled on ice, the reaction mixture was added with aqueous hydrochloric acid (1 N), and the mixture was stirred for 5 minutes, and further stirred for 30 minutes at room temperature. The deposited urea was removed by filtration under reduced pressure, and the filtrate was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, and treated in a conventional manner, and then the residue was purified by silica gel column chromatography [hexane/ethyl acetate (24:1 to 19:1)] to obtain benzyl 4-cyclopropyl(dimethyl)silyl-3-cyanobutanoate (7.50 g, 93%) mentioned in the title as colorless oil.

Provenance & Evidence