Hydrochloric Acid → Tetrahydrofuran-3-yl 4-methylbenzenesulfonate

HRID 571343Notes

Reaction equation

HRID 571343 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl>>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:6][CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 99603-Furanol, tetrahydro-

Product 1

HCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateYield 26%

Procedure

To a solution of tetrahydrofuran-3-ol (500 mg, 5.68 mmol) in Py (5 ml), 4-methylbenzene-1-sulfonyl chloride (1623 mg, 8.51 mmol) was added, and the mixture and stirred at Rt for 1 hour. The mixture was poured into HCl 1M and extracted with AcOEt (2×). The organic phase was dried over Na2SO4 and evaporated under reduced pressure to give 350 mg of the title compound (26% yield).

Workup

  1. extractionextracted with AcOEt (2×)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1967e4c8ceb948cab59880ef370c3199
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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