Selenious Acid → HCID 10686080, compound

HRID 2231096Notes

Reaction equation

HRID 2231096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Se](O)(O)=[O:22].O1CCOCC1>O>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9](=[O:22])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:20])=[CH:11][CH:12]=1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 1091Selenious AcidHCID 312751,4-DioxaneHCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Product 1

HCID 10686080HCID 10686080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ketone from step 3 (1 g, 3.5 mmol), selenious acid (H2SeO3) (550 mg, 1.25 equiv.), dioxane (10 ml) and water (1 ml) were heated to reflux for 4 hours and cooled. The mixture was filtered and the filtrate evaporated. The residue was triturated with cold methanol and filtered to give 620 mg (60%) of the dione: m.p. 174-175° C. Anal. Calc'd. for C15H11FO4S (M.W. 306.31): C, 58.82; H, 3.62; S, 10.47. Found: C, 58.70; H, 3.60; S, 10.70.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated
  6. customThe residue was triturated with cold methanol
  7. filtrationfiltered
  8. customto give 620 mg (60%) of the dione

Sources & evidence

ORD record
ord-024839bde96a484a9afd4d88861a4926
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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