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

HRID 581879Notes

Reaction equation

HRID 581879 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]1([CH2:17][CH2:18][OH:19])[CH2:16][CH2:15][CH2:14][CH:13]=1.N1C=CC=C[CH:21]=1>>[C:3]1([CH3:21])[C:4]([S:7]([O:19][CH2:18][CH2:17][C:12]2[CH2:16][CH2:15][CH2:14][CH:13]=2)(=[O:8])=[O:9])=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 128699622-(Cyclopent-1-en-1-yl)ethan-1-ol

Product 1

HCID 867542202-(Cyclopent-1-en-1-yl)ethyl toluenesulfonateYield 52.6%

Procedure

A para-toluenesulfonylchloride (3.81 g, 20 mmol) was added to the pyridine (30 ml) solution of 2-(cyclopent-1-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 (2.80 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-915aa0c8fc014c759814ec14fad93c82
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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