Dimethylformamide → 5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

11 g (24.7 mmol) of [(E)-5-(4-bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilane are dissolved in 100 mL of anhydrous THF and the mixture is cooled to −78° C. 10.9 mL (27 mmol) of 2.5 M butyllithium are added slowly and the mixture is stirred for 15 minutes. 2.1 mL (27 mmol) of dimethylformamide are then added and the medium is stirred for 30 minutes and then poured into aqueous ammonium chloride solution. After extraction with ethyl acetate and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate), the product is obtained in the form of a colourless oil (m=4 g; Y=41%).

Provenance & Evidence