4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 7303349, compound

Participants

Reaction Steps

To a solution of 4-methyl-5-thiazoleethanol (2 mL, 16.7 mmol) in CH2Cl2 (10 mL) and pyridine (10 mL) was added p-toluenesulfonyl chloride (3.5 g, 18.4 mmol) portionwise over 15 min. This mixture was stirred at ambient temperature for 18 h then was quenched with 5% aqueous HCl (15 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/ethyl acetate) to give 2-(4-methylthiazol-5-yl)ethyl 4-methylbenzenesulfonate (3.24 g, 10.9 mmol, 65% yield). MS (DCI/NH3) m/z 298 (M+H)+.

Provenance & Evidence