4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

HRID 1647852Notes

Reaction equation

HRID 1647852 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2]1.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(N(CC)CC)C>C1COCC1>[S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)([O:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 139980Tetrahydro-3-furanmethanol

Product 1

HCID 15335290Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 50 g of (tetrahydro-3-furanyl)methanol, 95 g of tosyl chloride, 52 g of triethylamine and 450 ml of THF was refluxed for 8 hours. After separation of insolubles by filtration, the reaction fluid was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 114.5 g of (tetrahydro-3-furanyl)methyl tosylate.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customAfter separation of insolubles
  3. filtrationby filtration
  4. concentrationthe reaction fluid was concentrated under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/7)

Sources & evidence

ORD record
ord-68a5b19ebc0749fabd2c8529193fd685
Source dataset
uspto-grants-1995_07
Patent number
US05434181

Reaction notes

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