Water → 1-[3-Chloro-4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-ethanone

HRID 1098755Notes

Reaction equation

HRID 1098755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=[O:17])[CH3:16])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[OH:18]OS([O-])=O.[K+].[OH2:24]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=[O:17])[CH3:16])[CH:5]=[CH:6][C:7]=1[S:8]([CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)(=[O:18])=[O:24]

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 595061481-[3-Chloro-4-(tetrahydro-pyran-4-ylsulfanyl)-phenyl]-ethanone

Product 1

HCID 595062921-[3-Chloro-4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-ethanoneYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product obtained from step 2 (1.38 g, 5.10 mmol) in methanol (25 ml) and tetrahydrofurane (25 ml) was added drop wise to a solution of oxone (5.64 g, 9.17 mmol) in water (25 ml) at 0° C. The suspension was stirred 2 days at RT. Water (25 ml) was added and the reaction mixture was extracted with DCM. The combined organic phases were washed with brine and dried over magnesium sulphate. Evaporation and purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (1.04 g, 67%).

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customEvaporation and purification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-db988866fb8f49d886201e663ac51506
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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