tert-Butyl methyl ether → HCID 178447843, compound

Participants

Reaction Steps

A suspension of 5.892 g of ethyltriphenylphosphonium bromide in 75 ml of tert.-butyl methyl ether was treated with 1.801 g of potassium tert.-butylate while stirring and gassing with nitrogen and stirred at room temperature for 1.5 hours. Subsequently, the suspension was treated dropwise at 2° C. within 45 minutes with a solution of 2.269 g of trans-4-(3',4'-difluoro-4-biphenylyl)cyclohexanecarboxaldehyde (prepared according to Example 3) in 17 ml of tert.-butyl methyl ether, stirred for a further 45 minutes and concentrated in a vacuum. The residue (9.7 g) was taken up in 50 ml of hexane, stirred and filtered. Concentration of the filtrate in a vacuum and chromatographical purification of the crude product obtained on silica gel with methylene chloride gave 2.464 g of 4-[trans-4-(propenyl)cyclohexyl]-3',4'-difluorobiphenyl (89.7% Z; 10.1% E).

Provenance & Evidence