Thiophenol → 6-Phenylsulfanyl-hexa-2,4-dienoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromohexa-2,4-dienoic acid methyl ester (0.57 g, 2.8 mmol) and thiophenol (0.28 mL, 2.8 mmol) was added triethylamine (0.43 mL, 3.1 mmol), dropwise, under an atmosphere of nitrogen. The mixture was stirred at 20° C. for one hour. The slurry was then filtered and the filtrate was washed with aqueous sodium hydroxide (1 M) then with brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to column chromatography (9:1 60-80° C. petroleum ether:diethyl ether) to give the title compound (0.93 g, 88%) as a clear oil.

Provenance & Evidence