Sulfuric Acid → HCID 15383994, compound

HRID 2393624Notes

Reaction equation

HRID 2393624 reaction equation
[Mg].[F:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.Br[CH:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24].S(=O)(=O)(O)O>IC.O1CCCC1>[F:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:22]2[CH2:27][CH2:26][O:25][C:23]2=[O:24])([OH:8])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 5462224MagnesiumHCID 10107581HCID 10107581, compound

Product 1

HCID 15383994HCID 15383994, compound

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (3.5 g) are covered with anhydrous tetrahydrofuran, and a few drops of iodomethane are added. As soon as the reaction has started, a mixture of 24.6 g of 4-fluoro-4'-methanesulfonylbenzophenone and 8.1 ml of α-bromo-γ-butyrolactone in 250 ml of anhydrous tetrahydrofuran is run in dropwise so as to maintain a gentle reflux. When the addition is complete, the reaction medium is cooled and then run into a mixture of ice and 10% dilute sulfuric acid. The organic phase is extracted with tetrahydrofuran, washed with saturated sodium bicarbonate solution and then dried over magnesium sulfate. After evaporation of the solvent, the residue obtained is chromatographed on silica gel with a 9/1 dichloromethane/acetone mixture to give 7 g of 3-[1-(4-fluorophenyl)-1-hydroxy-1-(4-methanesulfonylphenyl)methyl]dihydrofuran-2-one in the form of an amorphous beige powder, which is used as such in the next step.

Workup

  1. additionare added
  2. temperatureto maintain a gentle reflux
  3. additionWhen the addition
  4. temperaturethe reaction medium is cooled
  5. extractionThe organic phase is extracted with tetrahydrofuran
  6. washwashed with saturated sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. customAfter evaporation of the solvent
  9. customthe residue obtained
  10. customis chromatographed on silica gel with a 9/1 dichloromethane/acetone mixture

Sources & evidence

ORD record
ord-e3e8d2064cb74b128bf728e53097c140
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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