Pyridine → 2-Methoxypropyl 4-methylbenzenesulfonate

HRID 41234

Reaction equation

HRID 41234 reaction equation
ClCCl.[CH3:4][O:5][CH:6]([CH3:9])[CH2:7][OH:8].N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.O>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:8][CH2:7][CH:6]([O:5][CH3:4])[CH3:9])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 148462-Methoxy-1-propanol

Product 1

HCID 138965262-Methoxypropyl 4-methylbenzenesulfonateYield 71.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol).

Workup

  1. stirringthe mixture was stirred at room temperature for five hours
  2. stirringAfter thoroughly shaking the mixture
  3. customthe organic layer was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was filtered
  7. distillationthe solvent in the filtrate was then distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-a871361464a84328b4e7488902f129ec
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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