Ethyl 3-(3-bromophenyl)acrylate → 3-[3-(3-Thienyl)phenyl]-1-propanol

Participants

Reaction Steps

To a suspension (20 ml) of 0.4 g of lithium aluminum hydride in terahydrofuran was added, under ice cooling, a tetrahydrofuran solution (10 ml) of 2.1 g of ethyl (E)-3-(3-thienyl)cinnamate [synthesized by the same reaction as in Referential Example 12 using ethyl (E)-3-bromocinnamate [see Org. Syn. I, 252] and tri-n-butyl(3-thienyl)tin ]. The mixture was stirred at room temperature for 30 minutes, and then refluxed for 30 minutes. The solution was worked up in a customary manner, and the product was purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=5/1→5/2] to give 1.1 g of 3-[3-(3-thienyl)phenyl]-1-propanol as a pale yellow oil.

Provenance & Evidence