Pyridine → (Cyclopentyl)methyl toluenesulfonate

HRID 581867Notes

Reaction equation

HRID 581867 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1(C)[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.N1C=CC=C[CH:20]=1>>[C:10]1([CH3:20])[C:11]([S:14]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:16])=[CH:12][CH:13]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 77195Cyclopentanemethanol

Product 1

HCID 86754219(Cyclopentyl)methyl toluenesulfonateYield 74.7%

Procedure

To cyclopentanemethanol (2.0 g, 20 mmol) in pyridine (30 ml) was added para-toluenesulfonyl chloride (3.81 g, 20 mmol) with stirring. After 2 hrs at room temperature, the reaction mixture was concentrated for removement of pyridine, extracted with dichloromethane, dried, filtered, concentrated and separated by a column chromatography to give a desirable product (3.80 g).

Workup

  1. concentrationthe reaction mixture was concentrated for removement of pyridine
  2. extractionextracted with dichloromethane
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customseparated by a column chromatography

Sources & evidence

ORD record
ord-d0b5e88a91c04888b48e0b980482ae3c
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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