Water → HCID 66563009, compound

HRID 389293Notes

Reaction equation

HRID 389293 reaction equation
[OH:1][CH:2]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]2[S:10][C:11](=S)[S:12][C:4]=2[C:3]1=[O:14].[OH2:15]>CC(C)=O.C(O)(=O)C.[Hg](OC(C)=O)OC(C)=O>[OH:1][CH:2]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]2[S:10][C:11](=[O:15])[S:12][C:4]=2[C:3]1=[O:14]

Participants

6

Reactant 2

HCID 962WaterHCID 66562917HCID 66562917, compound

Product 1

HCID 66563009HCID 66563009, compound

Reagents, catalysts & solvents 3

HCID 16683746DiacetyloxymercuryCatalystHCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

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.

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2 (3×5 mL)
  2. customThe organic layer was separated
  3. washwas washed with saturated aqueous NaHCO3 (10 mL)
  4. customThe organic layer was separated again
  5. extractionthe aqueous layer was re-extracted again with CH2Cl2 (2×5 mL)
  6. customevaporated

Sources & evidence

ORD record
ord-c4812b4a41574a9dbe79c06285c53792
Source dataset
uspto-grants-2013_02
Patent number
US08378123B2

Reaction notes

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