Water → HCID 178442148, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 254 mg of 1-(trans-4-ethynylcyclohexyl)-4-pentylbenzene (prepared according to Example 12) in 60 ml of absolute tetrahydrofuran was placed at -45° C. in a 100 ml sulphonation flask under argon gasification and treated within 1 minute with 1.2 ml of a 1.0N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at -45° C. for a further 15 minutes, then cooled to -78° C. and treated with 182 μl of phenyl cyanate. The mixture was stirred at -78° C. for a further 90 minutes, then poured into 200 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed a further twice with 100 ml of water each time and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (380 mg) on silica gel with 2% ethyl acetate/petroleum ether gave 186 mg (66.6%) of trans-4-(p-pentylphenyl)cyclohexanepropiolonitrile as colourless crystals (purity 97.3%) which were recrystallized further from hexane (purity 99.3%); m.p. (C-I) 46.9° C., cl.p. (N-I) 45.4° C.

Provenance & Evidence