Sodium Iodide → dimethyl 4-[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienylmethoxy]phthalate

Participants

Reaction Conditions

Reaction Steps

3.9 g (9.8 mmol) of [5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienyl]methanol are dissolved in 100 mL of dichloromethane and the mixture is cooled to 0° C. 2 mL (15 mmol) of triethylamine are added, followed by 840 μL (10.7 mmol) of methanesulphonyl chloride. After stirring for 30 minutes, the medium is treated with ammonium chloride solution. The crude residue obtained is then dissolved in 100 mL of 2-butanone. 100 mg (0.7 mmol) of sodium iodide, 1.6 g (11.6 mmol) of potassium carbonate and 2 g (10 mmol) of dimethyl 4-hydroxyphthalate are added to this solution. The reaction medium is refluxed for 15 hours and then cooled and filtered through Celite. The residue obtained is purified by chromatography on a column of silica (eluent: 93 heptane/7 ethyl acetate). The desired product is obtained in the form of a colourless oil (m=1.7 g; Y=30%).

Provenance & Evidence