Sodium Thiosulfate → HCID 12889157, compound

HRID 1065741Notes

Reaction equation

HRID 1065741 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH3:7][CH2:8][S:9]([O:11][C:12]([CH:15]1[CH:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=2)[O:18][C:17](=[O:35])[CH2:16]1)([CH3:14])[CH3:13])=[O:10].S([O-])([O-])(=[O:38])=S.[Na+].[Na+]>CC(C)=O.O.C(O)(=O)C>[CH3:7][CH2:8][S:9]([O:11][C:12]([CH:15]1[CH:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=2)[O:18][C:17](=[O:35])[CH2:16]1)([CH3:13])[CH3:14])(=[O:38])=[O:10]

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 516875Potassium Permanganate2×HCID 12889155HCID 12889155, compound

Product 1

HCID 12889157HCID 12889157, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

0.084 g of potassium permanganate was added at 0° C. to a mixture of 0.214 g of trans dl 4-(2-ethylsulfinyloxy-isopropyl)-5-[(3-phenoxyphenyl)-methoxy]-tetrahydrofuran-2-one, 4 ml of acetone, 0.3 ml of acetic acid and 2 ml of water and the mixture was stirred at 0° C. for 2 hours. A solution of 0.050 g of potassium permanganate, 1 ml of water and 1 ml of acetone was added to the mixture which was then stirred at 0° C. for 17 hours and was poured into a sodium thiosulfate solution. The mixture was extracted with methylene chloride and the organic phase was washed with sodium bicarbonate solution and then with water, dried and evaporated to dryness without heating. The residue was chromatographed over silica gel and eluted with an 8-2 benzene-ethyl acetate mixture to obtain 0.090 g of trans dl 4-(2-ethyl-sulfonyloxy-isopropyl)-5-[(3-phenoxyphenyl)-methoxy]-tetrahydrofuran-2-one whose IR and NMR spectrum were identical to the compound of Example 1.

Workup

  1. stirringwas then stirred at 0° C. for 17 hours
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with sodium bicarbonate solution
  4. dry with materialwith water, dried
  5. customevaporated to dryness
  6. temperaturewithout heating
  7. customThe residue was chromatographed over silica gel
  8. washeluted with an 8-2 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-8280017139fa470fa1691183dd9c53b3
Source dataset
uspto-grants-1982_05
Patent number
US04331605

Reaction notes

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