Benzenesulfinic acid → 2-Benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran

Participants

Reaction Steps

To a solution of benzenesulphinic acid (8.68 g, 0.061 M) in DCM (120 ml) containing a suspension of CaCl2 (1.0 g) at room temperature was added a solution of 2-(3,4,dimethoxybenzyl)-5-methoxytetrahydrofuran (7.0 g, 0.029 M) in CH2Cl2 (80 ml). The mixture was stirred at room temperature for 4 h, quenched by washing with water (2×50 ml), dried (Na2SO4) and evaporated. Column chromatography (flash silica gel, hexane:ethyl acetate (3:2)) provided the product (Rf 0.3) as a clear oil which was crystallised from ethyl acetate/hexane to give 2-benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran (3.5 g, 35%).

Provenance & Evidence