Butyl iodide → HCID 178442125, compound

Participants

Reaction Steps

A solution of 1.42 g of β,β-dibromo-p-[2-(trans-4-pentylcyclohexyl)ethyl]styrene (prepared according to Example 5) in 32 ml of absolute tetrahydrofuran was placed at about 31 45° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 8.0 ml of a 1.2N solution of butyl lithium in hexane. After completed addition, the reaction mixture was stirred at this temperature for a further 90 minutes, before it was treated at -40° C. in sequence with 3.2 ml of hexamethylphosphoric acid triamide and 0.62 ml of butyl iodide. After warming to room temperature, the mixture was stirred for a further 24 hours, subsequently poured into 50 ml of water and extracted three times with 50 ml of petroleum ether each time. The organic phases were washed a further twice with 50 ml of water each time and once with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (1.07 g) on silica gel with hexane as the eluant gave 840 mg (81%) of 1-(1-pentynyl)-4-[2-(trans-4-pentylcyclohexyl)ethyl]benzene as colourless crystals (purity according to gas chromatography 98.3%). Recrystallization from 75 ml of methanol yielded 634 mg of 1-(1-pentynyl)-4-[2-(trans-4-pentylcyclohexyl)ethyl]benzene with m.p. (C-I) 37.8° C. and cl.p. (S-I) 30.9° C.

Provenance & Evidence