Sodium Thiosulfate → 2,2-dimethyl-4-(4-hydroxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298311Notes

Reaction equation

HRID 2298311 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[O:3]1.B(Br)(Br)Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:26])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[O:3]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 25134Boron tribromideHCID 183855972,2-dimethyl-4-(4-methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Product 1

HCID 183858172,2-dimethyl-4-(4-hydroxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 mg of 2,2-dimethyl-4-(4methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (Example 3) in 30 ml dichloromethane was stirred with 0.1 ml boron tribromide (1.0 M solution in CH2Cl2) at room temperature for 4 hours. And then 10 ml aqueous sodium thiosulfate was added to the reaction mixture. The mixed solution was concentrated in vacuo and was extracted with 50 ml water and dichloromethane (50 ml×3). The organic layer was concentrated under reduced pressure and was purified by column chromatography (ethylacetate) to afford 25 mg of 2,2-dimethyl-4-(4-hydroxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. mp: 150-152° C. NMR: δ1.56 (s, 6H), 2.77 (s, 1H), 3.07 (s, 3H), 6.81 (d, J=8.7 Hz, 2H), 7.14 (d, J=8.7 Hz, 2H), 7.90 (m, 4H). IR (cm−1): 3492, 2929, 1696, 1597, 1393, 1151, 914, 744.

Workup

  1. concentrationThe mixed solution was concentrated in vacuo
  2. extractionwas extracted with 50 ml water and dichloromethane (50 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (ethylacetate)

Sources & evidence

ORD record
ord-0ed3f3818a5b4ae9a3d981045759cf02
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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