Water → HCID 15036005, compound

HRID 2371934Notes

Reaction equation

HRID 2371934 reaction equation
[F:1][C:2]([F:24])([F:23])[S:3][C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH3:20])([CH3:19])[C@@H:10]([OH:18])[C@H:11]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[C:6]=2[CH:5]=1.[OH:25]OS([O-])=O.[K+].[OH2:31]>CO>[F:24][C:2]([F:1])([F:23])[S:3]([C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH3:20])([CH3:19])[C@@H:10]([OH:18])[C@H:11]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[C:6]=2[CH:5]=1)(=[O:25])=[O:31].[F:24][C:2]([F:1])([F:23])[S:3]([C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH3:20])([CH3:19])[C@@H:10]([OH:18])[C@H:11]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[C:6]=2[CH:5]=1)=[O:25]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 67697900HCID 67697900, compound

Product 2

HCID 15036005HCID 15036005, compoundYield 55%HCID 67918239HCID 67918239, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g (5.5 mmol) of 6-trifluoromethylthio-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo(b)pyran-3-ol are dissolved in 7 ml of methanol and a suspension of 1 g of Oxone® in 5 ml of water is added at 0° C. with stirring. After stirring for 5 days at room temperature, the mixture is diluted using 20 ml of water and extracted using chloroform (3×50 ml). After drying and evaporating, 0.2 g of white crystals remain. By means of HPLC (eluent chloroform:methanol 98:2), 120 mg (55% of theory) of 6-trifluoromethylsulphonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo(b)pyran-3-ol and 15 mg of 6-trifluoromethylsulphinyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo(b)-pyran-3-ol are obtained.

Workup

  1. additionis added at 0° C.
  2. stirringAfter stirring for 5 days at room temperature
  3. additionthe mixture is diluted
  4. extractionextracted
  5. customAfter drying
  6. customevaporating

Sources & evidence

ORD record
ord-8aaafe4228d248e694e06f84bb36d58b
Source dataset
uspto-grants-1992_03
Patent number
US05096914

Reaction notes

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