Tetrabutylammonium Fluoride → dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalate

Participants

Reaction Conditions

Reaction Steps

750 mg (1.3 mmol) of dimethyl 4-[5-((E)-5-ethyl-1-methyl-5-triethylsilanyloxyhept-1-enyl)-2-thienylmethoxy]phthalate are dissolved in 30 mL of THF. 2.6 mL (2.6 mmol) of a 1.0 M tetrabutylammonium fluoride solution are added and the reaction medium is heated at 60° C. for 3 hours. After treatment with ammonium chloride solution and extraction with ethyl acetate, the organic phases are combined, dried and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica. A yellow oil is obtained (m=355 mg; Y=59%).

Provenance & Evidence