Water → HCID 67698203, compound

HRID 2371933Notes

Reaction equation

HRID 2371933 reaction equation
[F:1][C:2]([F:25])([F:24])[S:3][C:4]1[CH:23]=[CH:22][C:7]2[O:8][C:9]([CH3:21])([CH3:20])[C@@H:10]([OH:19])[C@H:11]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3=[O:18])[C:6]=2[CH:5]=1.[OH:26]OS([O-])=O.[K+].[OH2:32]>CO>[F:25][C:2]([F:1])([F:24])[S:3]([C:4]1[CH:23]=[CH:22][C:7]2[O:8][C:9]([CH3:20])([CH3:21])[C@@H:10]([OH:19])[C@H:11]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3=[O:18])[C:6]=2[CH:5]=1)(=[O:26])=[O:32].[F:25][C:2]([F:1])([F:24])[S:3]([C:4]1[CH:23]=[CH:22][C:7]2[O:8][C:9]([CH3:20])([CH3:21])[C@@H:10]([OH:19])[C@H:11]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3=[O:18])[C:6]=2[CH:5]=1)=[O:26]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 67697850HCID 67697850, compound

Product 2

HCID 67698203HCID 67698203, compoundYield 64%HCID 67918180HCID 67918180, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g (5.3 mmol) of 6-trifluoromethylthio-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-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 (50 ml). After drying and evaporating, 220 mg of white crystals remain. By means of HPLC (eluent 98:2 chloroform:methanol), 140 mg (64% of theory) of 6-trifluoromethylsulphonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo(b)pyran-3-ol and 15 mg (7% of theory) of 6-trifluoromethylsulphinyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-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-f861cf81201b4b068f5ca44b3ca112fe
Source dataset
uspto-grants-1992_03
Patent number
US05096914

Reaction notes

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