Water → HCID 66563009, compound

Participants

Reaction Steps

13 mg (0.05 mmol) of 6-hydroxy-4,4-dimethyl-2-thioxo-4H-[1,3]dithiolo[4,5-c]pyran-7(6H)-one 6 was dissolved in acetone (5 mL) and added to a solution of Hg(OAc)2 (50 mg, 0.15 mmol) in 1 ml of acetic acid. The color of the reaction mixture changed very fast from yellow to white. The solution was stirred for 10 minutes and then 20 mL of water was added. The resulting mixture was extracted with CH2Cl2 (3×5 mL). The organic layer was separated and then was washed with saturated aqueous NaHCO3 (10 mL) The organic layer was separated again and the aqueous layer was re-extracted again with CH2Cl2 (2×5 mL). The organic layers were combined and evaporated to get 6-hydroxy-4,4-dimethyl-4H-[1,3]dithiolo[4,5-c]pyran-2,7(6H)-dione 8 as a pale beige oil. Yield: 7 mg (0.03 mmol, 57%). 1H NMR in CDCl3 (δ, ppm): 5.51 (1H, s, hemiacetal), 1.74 (3H, s, CH3), 1.68 (3H, s, CH3). 13C NMR in CDCl3 (δ, ppm): 187.09, 181.81, 159.93, 124.38, 91.15, 76.16, 31.47, 28.27. IR (neat, cm−1): 3419, 2978, 2929, 2864, 1670, 1625, 1548.

Provenance & Evidence