Water → HCID 178444311, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.2 g of 1-ethynyl-4-(trans-4-pentylcyclohexyl)benzene (prepared according to Example 3) in 50 ml of absolute tetrahydrofuran was placed at -40° C. in a sulphonation flask under argon gasification and treated with 4.72 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -40° C. for a further 15 minutes, subsequently treated at -78° C. with 1.07 ml of phenyl cyanate and stirred at -78° C. for a further 45 minutes. The mixture was then poured into 50 ml of water and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the crystalline residue on silica gel with 3% ethyl acetate/petroleum ether gave 1.20 g (91%) of p-(trans-4-pentylcyclohexyl)phenylpropiolonitrile as colourless crystals (purity 99.6%). A single crystallization from 50 ml of methanol yielded 687 mg of the product with m.p. (C-N) 49.7° C. and cl.p. (N-I) 128.9° C.

Provenance & Evidence