Homoallyl bromide → HCID 178444522, 화합물

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A suspension of 9.14 g of copper(I) iodide in 90 ml of tetrahydrofuran was treated within 5 minutes at 78° C. with 25.7 ml of 1.5M solution of methyl lithium in tetrahydrofuran using a syringe. The suspension was stirred for a further 45 minutes at -78° C., then left to warm to 0° C. and stirred for a further 3 minutes at 0° C. Thereafter, the suspension was again cooled to -78° C. and treated within 5 minutes using a steel cannula with a Grignard solution prepared from 4.56 ml of 4-bromo-1-butene and 1.1 g of magnesium in 60 ml of tetrahydrofuran. The suspension was stirred for a further 20 minutes at -78° C., then left to warm to 15° C. and stirred for a further 5 minutes at 15° C. Thereafter, the solution was again cooled to -78° C. and treated dropwise within 5 minutes with a solution of 4.8 g of trans-4-(iodomethyl)cyclohexanecarbonitrile in 30 ml of tetrahydrofuran. Thereafter, the reaction mixture was left to warm and was stirred for a further 30 minutes at 16° C. Subsequently, the reaction mixture was treated cautiously in a cooling bath with about 50 ml of ammonium chloride solution and partitioned in methylene chloride/ammonium chloride solution. The aqueous phase was extracted three times with methylene chloride. The organic phases were washed once with ammonium chloride solution and twice with water, dried over magnesium sulphate, filtered and concentrated. Chromatographic separation of the yellow, oily residue (3.4 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 2.9 g (85%) of trans-4-(4-pentenyl)cyclohexanecarbonitrile as a light yellow oil.

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