Tetrabutylammonium Fluoride → 3-Ethynyl-4,5-dimethoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,4-dimethoxy-5-(trimethylsilanylethynyl)benzoic acid (5.56 g, 20 mmol) in THF (115 mL) at 0° C. was added TBAF (1.0 M solution in THF, 30 mL, 30 mmol). The resulting solution was stirred at 0° C. for 30 min, then the reaction mixture was diluted with 1 N HCl aqueous solution (200 mL), extracted with EtOAc (3×70 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo to give 3-ethynyl-4,5-dimethoxybenzoic acid (4.0 g). The product was used without further purification.

Provenance & Evidence