4-Toluenesulfonyl chloride → Tetrahydrofuran-3-yl 4-methylbenzenesulfonate

HRID 659882Notes

Reaction equation

HRID 659882 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>N1C=CC=CC=1>[O:4]1[CH2:5][CH2:6][CH:2]([O:1][S:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:3]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 99603-Furanol, tetrahydro-

Product 1

HCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateYield 51.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-hydroxy tetrahydrofuran (2.5 g, 28.0 mmol) in anhydrous pyridine (60 mL) at room temperature was added 4-toluene sulfonyl chloride (6.49 g, 34.0 mmol). After stirring the reaction mixture for 18 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane to afford 3.5 g (51% yield) of the desired product as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-7d554f9d21724535ada5b6cbe118cf87
Source dataset
uspto-grants-2011_12
Patent number
US08080580B2

Reaction notes

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