Water → 3-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropane

HRID 440192Notes

Reaction equation

HRID 440192 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[Na+].O>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+]>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:2][CH2:3][CH2:4][O:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 962WaterHCID 2723791Sodium p-toluenesulfinateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 220761783-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropaneYield 76%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

32 g (144 mmol) of 3-bromo-1-tetrahydropyranyloxypropane (1a) are dissolved in 200 ml of 1,2-dimethoxyethane, 26.9 g (151 mmol) of anhydrous sodium 4-methylphenyl-sulfinate, 4.5 g (14 mmol) of tetrabutylammoniumbromide and 1.05 g (7 mmol) of sodium iodide are added and the mixture is heated to boiling for 24 hours. After cooling, 500 ml of water are added, the mixture is extracted with three times 300 ml of dichloromethane each time, the combined dichloromethane extracts are washed with water and dried with magnesium sulfate. After filtering off the drying agent and distilling off the solvent in vacuo a yellowish brown oil is obtained which is purified by column chromatography (silica gel; dichloromethane or dichloromethane/ethyl acetate mixtures). 32.5 g (76%) of a colorless oil are isolated, which partly crystallizes on prolonged standing (m.p.<30° C.)

Workup

  1. temperaturethe mixture is heated
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with three times 300 ml of dichloromethane each time
  4. washthe combined dichloromethane extracts are washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationdistilling off the solvent in vacuo a yellowish brown oil
  8. customis obtained which
  9. customis purified by column chromatography (silica gel; dichloromethane or dichloromethane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-f8f90895a701458faf0af04f319daf24
Source dataset
uspto-grants-1996_05
Patent number
US05517350

Reaction notes

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