Hydrochloric Acid → Tert-butyl 2-methylthio-6-n-hexylcinnamate

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide, afforded by combining 3.4 g of diisopropylamine with 26 ml of n-butyllithium, at -40° C. in THF is added tert-butyl trimethylsilylacetate (8 g, 0.042 mmol) and the mixture stirred for 1 hour. To the reaction mixture is added 2-methylthio-6-n-hexylbenzaldehyde (7.08 g, 0.03 mmol) dropwise and stirred for 2 hours at -40° C. The reaction mixture is allowed to warm to -10° C. and cold lN HCl poured in. The mixture is extracted with diethyl ether. The extracts are washed with water and then brine, dried over MgSO4 and concentrated to afford tert-butyl 2-methylthio-6-n-hexylcinnamate which is hydrolyzed in methylene chloride with trifluoroacetic acid by refluxing overnight to afford the subtitle compound.

Provenance & Evidence