Hydrochloric Acid → 4-Mercapto-1-Methyl-tetrahydrothiopyraniumtriflate

Participants

Reaction Conditions

Reaction Steps

To a cooled (5° C.) solution of 4-acetylthio-1-methyltetrahydrothiopyranium trifluoromethanesulfonate (3.35 g, 9.83 mmol) in deoxygenated water (32 mL) was added a solution of 1M NaOH (10.8 mL, 10.8 mmol) dropwise. After stirring for 1 hr at 0° C., the pH was adjusted to 7.5 with 1N HCl. The solution was lyophylized to give the desired thiol plus a mixture of salts. The product was used as such without further purification: 1Hmr (D2O) δ: 2.0-4.0 (m, 11H), 2.90 (s, 3H, SCH3) and 1.9 ppm (s, 3H, CH3CO-).

Provenance & Evidence