Water → HCID 178445833, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.5 g of trans-2-[p-(2,2-dibromovinyl)phenyl]-5-butyl-1,3-dioxane in 80 ml of absolute tetrahydrofuran was placed at -78° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 13.4 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was held at -10° C. for 1 hour, then again cooled to -78° C. and treated with 1.2 ml of phenyl cyanate within 5 minutes. The mixture was stirred at -78° C. for a further 30 minutes, then poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed with 100 ml of water and 100 ml of saturated sodium chloride solution, dried over potassium carbonate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.26 g) on silica gel with petroleum ether/ethyl acetate/triethylamine (97:3:0.2) gave 1.18 g (50%) of p-(trans-5-butyl-1,3-dioxan-2-yl)phenylpropiolonitrile (purity 98.7%). A recrystallization from 50 ml of hexane yielded 1.03 g of the nitrile as colourless crystals (purity 99.7%); m.p. (C-N) 54.3° C., cl.p. (N-I) 108.7° C.

Provenance & Evidence