Hydrochloric Acid → HCID 54499594, compound

Participants

Reaction Steps

A mixture of 50 g of 4-n-pentyl-4-phenyl-4-silacyclohexanecarboxylic acid, 50.0 g of triphenylphosphine and 420 ml of carbon tetrachloride was agitated under reflux for 1 hour. Then, a mixture of 32.0 g of 4-trifluoromethoxyphenol and 100 ml of pyridine was added to the mixture, followed by further addition of 1.00 g of 4-dimethylaminopyridine and agitation at room temperature for 9 hours. The resultant reaction mixture was poured into dilute hydrochloric acid, followed by extraction with ethyl acetate. The ethyl acetate solution was washed with brine, dried and concentrated, followed by purification of the resultant residue with silica gel chromatography to obtain 60.8 g (yield: 78%) of (4-trifluoromethoxyphenyl) 4-n-pentyl-4-phenyl-4-silacyclohexanecarboxylate. The results of IR and NMR analyses are shown below.

Provenance & Evidence