Pyridine → 2-(Cyclopent-3-en-1-yl)ethyl toluenesulfonate

HRID 581881

Reaction equation

HRID 581881 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]1([CH2:17][CH2:18][OH:19])[CH2:16][CH:15]=[CH:14][CH2:13]1.N1C=CC=C[CH:21]=1>>[C:3]1([CH3:21])[C:4]([S:7]([O:19][CH2:18][CH2:17][CH:12]2[CH2:16][CH:15]=[CH:14][CH2:13]2)(=[O:8])=[O:9])=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 157490023-Cyclopentene-1-ethanol

Product 1

HCID 867542212-(Cyclopent-3-en-1-yl)ethyl toluenesulfonateYield 60.8%

Procedure

A para-toluenesulfonylchloride (3.81 g, 20 mmol) was added to the pyridine (30 ml) solution of 2-(cyclopent-3-en-1-yl)ethyl alcohol (2.24 g, 20 mmol) and then the reaction mixture was stirred at room temperature for 2 hrs. After the removement of pyridine, the residue was extracted with dichloromethane, washed with 1N HCl, dried, filtered and separated by column chromatography to give a desirable product (3.24 g).

Workup

  1. extractionAfter the removement of pyridine, the residue was extracted with dichloromethane
  2. washwashed with 1N HCl
  3. customdried
  4. filtrationfiltered
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-33cf5353fbfa4e159987f8de76ce1c8d
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Linked notes

Loading…