Methanol → HCID 57675682, compound

HRID 490954Notes

Reaction equation

HRID 490954 reaction equation
[C:1]1([S:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[CH2:13]CO3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][OH:20].[OH:21]OS([O-])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[OH2:35]>>[C:1]1([S:7]([C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[CH2:13][CH2:19][O:20]3)=[CH:10][CH:9]=2)(=[O:21])=[O:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 57302114HCID 57302114, compound

Product 1

HCID 57675682HCID 57675682, compoundYield 63%

Procedure

A solution of 7-phenylsulfanyl-chroman-4-one (2.21 g, 8.62 mmol) in 20 mL o MeOH and 2 mL water was stirred at room temperature. OXONE™ (potassium peroxymonosulfate, 6.35 g, 10.35 mmol) was added, and the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, and solvent was evaporated under reduced pressure. The resulting residue was eluted through silica gel with 35% EtOAc in hexanes. Removal of solvent under reduced pressure afforded 1.56 g (5.41 mmol, 63%) of 7-benzenesulfonyl-chroman-4-one. MS: 289 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over MgSO4, and solvent
  3. customwas evaporated under reduced pressure
  4. washThe resulting residue was eluted through silica gel with 35% EtOAc in hexanes
  5. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-df0c01b6cdac475393980d3530f30082
Source dataset
uspto-grants-2009_05
Patent number
US07528250B2

Reaction notes

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