Hexane → HCID 178444459, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4.4 g of tetrabromomethane in 80 ml of methylene chloride was placed at -15° C. in a sulphonation flask under argon gasification and treated within 5 minutes with a solution of 7.0 g of triphenylphosphine in 20 ml of methylene chloride. The clear deep orange solution was stirred at -5° C. for a further 10 minutes and then a solution of 1.95 g of the trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarboxaldehyde in 20 ml of methylene chloride was added dropwise within 10 minutes. The mixture was stirred at 0° C. for a further 30 minutes, then poured into 600 ml of hexane and the precipitate which thereby separated was filtered off (rinsing with hexane). The concentrated filtrate was digested with 300 ml of hexane, left to stand at 0° C. for 30 minutes, filtered (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.0 g) on silica gel with hexane gave 2.68 g (89.2%) of trans-1-(2,2-dibromovinyl)-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexane which contained about 10% of the corresponding epimeric cis compound in accordance with NMR spectroscopic analysis and which was used without additional purification.

Provenance & Evidence