tert-Butanol → t-Butyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate

Participants

Reaction Steps

A solution of dicyclohexylcarbodiimide (0.124 g) in THF (1 ml) was added dropwise to a mixture of 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoic acid (Intermediate 114, 0.358 g) and 4-dimethylaminopyridine (0.0032 g) and t-butanol (3 ml) in THF (1 ml). The resultant mixture was stirred at room temperature for 4 hours. The solid was removed by filtration and the filtrate was washed with citric acid (5% aqueous solution), sodium bicarbonate (saturated aqueous solution) and brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (20%) to give t-butyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (0.19 g) as a waxy white solid.

Provenance & Evidence