Water → HCID 18386004, compound

HRID 2298305Notes

Reaction equation

HRID 2298305 reaction equation
[Br:1][C:2]1[C:6](=[O:7])[C:5]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[O:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15](SC)=[CH:14][CH:13]=1.O[O:21][S:22]([O-:24])=O.[K+].[CH2:26]1COCC1.O>C(O)C>[Br:1][C:2]1[C:6](=[O:7])[C:5]2([CH2:8][CH2:9][CH2:10][CH2:11]2)[O:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([S:22]([CH3:26])(=[O:24])=[O:21])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18385639HCID 18385639, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18386004HCID 18386004, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 mg of 3-bromo-2-{4-(methylthio)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one was stirred with 292 mg of OXONE at room temperature overnight in 5 ml ethanol, 5 ml THF, and 5 ml water. Then the insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The resulting aqueous layer was extracted with dichloromethane and the organic layer was concentrated in vacuo. The resulting residue was purified to column chromatography (hexane/ethylacetate) to afford 68 mg of 3-bromo-2-{4-(methylsulfonyl)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one as a solid. mp: 127-128° C. NMR: δ1.98 (m, 6H), 2.12 (m, 2H), 3.11 (s, 3H), 8.09 (d, J=8.7 Hz, 2H), 8.37 (d, J=8.7 Hz, 2H).

Workup

  1. filtrationThen the insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionThe resulting aqueous layer was extracted with dichloromethane
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe resulting residue was purified to column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-80f2c0e1a85f450cbaab5cae47e890aa
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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