4-Toluenesulfonyl chloride → HCID 67003408, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of 2-(4-methoxybenzyloxy)-2-(thiazol-2-yl)propane-1,3-diol (Example 11C) (4.02 g, 13.61 mmol) in tetrahydrofuran (120 mL) was added n-butyllithium (5.4 mL, 13.6 mmol, 2.5 M solution in hexane) dropwise. After 0.5 hours, a solution of para-toluenesulfonyl chloride (2.59 g, 13.61 mmol) in tetrahydrofuran (16 mL) was added to the suspension. The reaction was stirred for an additional 0.5 hours. Thereafter, n-butyllithium (5.4 mL, 13.6 mmol, 2.5 M solution in hexane) was added to the reacton dropwise, and the reaction was heated to 65° C. for 1 hour. The reaction was cooled to room temperature and quenched by the addition of water and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 30% ethyl acetate in hexane, to give the title product. MS ESI(+) m/z 278.3 [M+H]+;

Provenance & Evidence