Potassium sodium tartarate → HCID 178444462, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.3 g of trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarbonitrile in 100 ml of methylene chloride was placed at -78° C. in a sulphonation flask under argon gasification and treated within 3 minutes with 10.5 ml of a 1.5M solution of diisobutylaluminium hydride in toluene. The mixture was subsequently stirred at -78° C. for a further 4 hours, then treated cautiously with 50 ml of 10% potassium sodium tartrate solution and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed 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 (2.1 g) on silica gel with 5% ethyl acetate/petroleum ether gave 1.95 g (84.4%) of trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarboxaldehyde which contained about 10% of the corresponding epimeric cis aldehyde in accordance with NMR spectroscopic analysis and which was reacted without additional purification.

Provenance & Evidence