trans-3,4-Dihydro 2,2-dimethyl-4-(1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol → 2,2-Dimethyl-4-(1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran

HRID 1656454Notes

Reaction equation

HRID 1656454 reaction equation
[CH3:1][C:2]1([CH3:30])[C@@H:7](O)[C@H:6]([N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:18])[C:5]2[CH:19]=[C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[CH:21]=[CH:22][C:4]=2[O:3]1>O1CCOCC1>[CH3:1][C:2]1([CH3:30])[CH:7]=[C:6]([N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:18])[C:5]2[CH:19]=[C:20]([S:23]([C:26]([F:29])([F:27])[F:28])(=[O:25])=[O:24])[CH:21]=[CH:22][C:4]=2[O:3]1

Participants

3

Reactant 1

HCID 14748246trans-3,4-Dihydro 2,2-dimethyl-4-(1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol

Product 1

HCID 197881002,2-Dimethyl-4-(1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyranYield 42.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

200 mg of soda talc (Merck Catalog No. 1567) were added to a solution of 200 mg of trans-3,4-dihydro-2,2-dimethyl-4-(1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol (prepared as described in Preparation 13) in 6 ml of dioxane, and the resulting mixture was stirred for 30 minutes whilst heating it on an oil bath kept at 140° C. The reaction mixture was cooled and then freed from insoluble materials by filtration. The solvent was then removed by distillation under reduced pressure. The residue was dissolved in 20 ml of methylene chloride, and the resulting solution was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The solution was dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The oily residue thus obtained was recrystallized from ethyl acetate, to afford 81 mg of the title compound, melting at 110°-115° C.

Workup

  1. temperaturewhilst heating it on an oil bath
  2. customkept at 140° C
  3. temperatureThe reaction mixture was cooled
  4. filtrationfreed from insoluble materials by filtration
  5. customThe solvent was then removed by distillation under reduced pressure
  6. dissolutionThe residue was dissolved in 20 ml of methylene chloride
  7. washthe resulting solution was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  8. dry with materialThe solution was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe oily residue thus obtained
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7648c31087434db99428adee79b5899e
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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