Tetrahydrofuran → HCID 18386141, compound

HRID 2298320Notes

Reaction equation

HRID 2298320 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:12](=[O:14])[CH:13]=2)=[CH:5][CH:4]=1.O[O:21][S:22]([O-:24])=O.[K+].[CH2:26]1COCC1>C(O)C.O>[CH3:26][S:22]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:12](=[O:14])[CH:13]=2)=[CH:5][CH:4]=1)(=[O:24])=[O:21]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 18385591HCID 18385591, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18386141HCID 18386141, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-{4-(methylthio)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one (0.6 g) in 10 ml THF and 10 ml ethanol, was added 2.67 g of OXONE dissolved in 5 ml water. The mixture was stirred for 26 hours at room temperature. After volatile solvent was evaporated in vacuo, the aqueous solution was extracted with dichloromethane. The organic layer was concentrated under reduced pressure and the resulting crude product was purified by recrystallization from hexane/dichloromethane to give 0.55 g of 2-{4-(methylsulfonyl)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one. mp: 163-165° C. NMR: δ1.58-1.70 (m, 2H), 2.09-2.20 (m, 2H), 3.11 (s, 3H), 3.82-3.92 (m, 2H), 4.04-4.14 (m, 2H), 6.16 (s, 1H), 8.05 (d, J=8.7 Hz, 2H), 8.10 (d, J=8.7 Hz, 2H). IR (cm−1): 2862, 1694, 1314, 1152, 961.

Workup

  1. customAfter volatile solvent was evaporated in vacuo
  2. extractionthe aqueous solution was extracted with dichloromethane
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting crude product was purified by recrystallization from hexane/dichloromethane

Sources & evidence

ORD record
ord-3f64dd5a91b5424899e7f2de3554d614
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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