Water → Tetrahydrofuran-3-yl 4-methylbenzenesulfonate

HRID 41231

Reaction equation

HRID 41231 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.N1C=CC=CC=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[O:4]1[CH2:5][CH2:6][CH:2]([O:1][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 99603-Furanol, tetrahydro-

Product 1

HCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateYield 67.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a mixture of 3-hydroxytetrahydrofuran (7.00 g, 79.5 mmol) and pyridine (100 mL), was added p-toluenesulfonyl chloride (18.2 g, 95.4 mmol) while stirring at room temperature, and the resulting mixture was stirred for 8.5 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 then the solvent in the filtrate was 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=4/1) to obtain the title compound (13.0 g, 53.7 mmol).

Workup

  1. stirringthe resulting mixture was stirred for 8.5 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 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-872bb89e4f994941b3711d549ccabc83
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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