4-Toluenesulfonyl chloride → HCID 57076460, compound

Participants

Reaction Steps

To a solution of 2-[5-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)phenyl]propan-2-ol (Intermediate 10, 1.344 g, 4.533 mmol) in THF (5 mL) at 0° C. butyllithium 1.6M in hexane (3.116 ml, 4.98 mmol) was added and the reaction mixture was stirred for 5 minutes at the same temperature. 4-methylbenzenesulfonyl chloride (1.04 g, 5.44 mmol) dissolved in 1 ml of THF was added followed by the addition of butyllithium 1.6M in hexane (3.116 ml, 4.98 mmol). After 10 minutes at the same temperature tetrabutylammonium fluoride (9.066 ml, 9.066 mmol) was added and the reaction mixture stirred for additional 10 min. Then, it was quenched with ammonium chloride (50 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with brine (2×100 ml), dried with Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage system) using a SNAP 50 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 to afford the title compound (500 mg) as white solid

Provenance & Evidence