Tetrahydrofuran → [5-((e)-5-Ethyl-1-methyl-5-triethylsilanyloxyhept-1-enyl)-2-thienyl]methanol

Participants

Reaction Conditions

Reaction Steps

2.8 g (6.5 mmol) of [(E)-5-(5-bromo-2-thienyl)-1,1-diethylhex-4-enyloxy]triethylsilane are dissolved in 50 mL of anhydrous THF and the mixture is then cooled to −78° C. 2.9 mL (7.1 mmol) of 2.5 M butyllithium solution are then added, after which the reaction medium is stirred for 15 minutes. 0.55 mL of anhydrous DMF is then added, after which the reaction medium is warmed to room temperature and stirred for 1 h. After treatment with saturated ammonium chloride solution and then extraction with ethyl acetate, the organic phases are combined, dried and concentrated under reduced pressure. The residue containing the desired 5-((E)-5-ethyl-1-methyl-5-triethylsilanyloxyhept-1-enyl)thiophene-2-carbaldehyde is then dissolved in 50 mL of anhydrous methanol, after which 150 mg (3.9 mmol) of sodium borohydride are added in two portions. After stirring for 10 minutes, the medium is treated with ammonium chloride solution and extracted with ethyl ether. The organic phases are combined, dried and concentrated under reduced pressure. After purification by chromatography on a column of silica, a yellow oil is obtained (m=1.76 g; Y=71%).

Provenance & Evidence