Water → 3-(4-(Methanesulfonyl)phenyl)-2-phenylinden-1-one

HRID 2269572Notes

Reaction equation

HRID 2269572 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1.C1C=C(C([O-])=[O:32])C(C(O[O-])=O)=CC=1.[Mg+2].[OH2:39].C([O-])(O)=O.[Na+]>C(Cl)Cl.CO.CCOC(C)=O>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:7][CH:8]=1)(=[O:32])=[O:39]

Participants

8

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 15337399HCID 15337399, compound

Product 1

HCID 153373963-(4-(Methanesulfonyl)phenyl)-2-phenylinden-1-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of the compound from Step 1 (525 mg, 1.6 mmol) in CH2Cl2 (16 mL) and MeOH (1.6 mL) was added MMPP (1.09 g, tech. 80%, 1.76 mmol). The resulting suspension was stirred at r.t. for 3 hrs. The reaction was diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified first by flash chromatography, eluted with EtOAc in hexane 35%, and then crystallized from EtOAc/Hexane (1:1, 20 mL) to give the title compound as a bright orange solid. m.p. 167-168° C.

Workup

  1. extractionextracted
  2. extractionThe aqueous layer was extracted one more time with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified first by flash chromatography
  6. washeluted with EtOAc in hexane 35%
  7. customcrystallized from EtOAc/Hexane (1:1, 20 mL)

Sources & evidence

ORD record
ord-d0dad51fc36c49f4a84ddd52678b9c93
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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