Pyridine → Tetrahydrofuran-3-yl 4-methylbenzenesulfonate

HRID 256282Notes

Reaction equation

HRID 256282 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.N1C=CC=CC=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:1][CH:2]2[CH2:6][CH2:5][O:4][CH2:3]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 3

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

Product 1

HCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateYield 80.3%

Procedure

A stirred solution of 10.0 g (0.11 mole) of 3-hydroxytetrahydrofuran in 36.0 g (0.46 mole) of pyridine was cooled in an ice bath and 22.0 g (0.12 mole) of 4-methylphenylsulfonyl chloride was added. Upon complete addition, the reaction mixture was stirred at ambient temperature for 60 hours. The reaction mixture was poured into ice-water, and the mixture extracted with diethyl ether. The combined ether extracts were washed several times with water. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 21.4 g of 3-tetrahydrofuranyl 4-methylphenylsulfonate.

Workup

  1. additionUpon complete addition
  2. extractionthe mixture extracted with diethyl ether
  3. washThe combined ether extracts were washed several times with water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-16afede9edb4446c86191f38b19e5afc
Source dataset
uspto-grants-1987_10
Patent number
US04702763

Reaction notes

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