Pyridine → Cyclopentylmethyl 4-methylbenzene-1-sulfonate

HRID 968638Notes

Reaction equation

HRID 968638 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 77195Cyclopentanemethanol

Product 1

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentanemethanol p-toluenesulfonate was prepared by the following method: To a solution of cyclopentanemethanol (2.0 g, 20.0 mmol) and pyridine (2.9 ml, 36.3 mmol) in dichloromethane (20 ml) was added p-toluenesulfonyl chloride (3.46 g, 18.1 mmol). The mixture was stirred at room temperature for 24 h under nitrogen. The resulting mixture was washed with 2M hydrochloric acid and the aqueous layer separated and extracted with dichloromethane. The combined organics were dried over sodium sulphate and concentrated under reduced pressure to yield cyclopentanemethanol p-toluenesulfonate as a colourless oil (4.3 g, 17.0 mmol).

Workup

  1. customCyclopentanemethanol p-toluenesulfonate was prepared by the following method
  2. washThe resulting mixture was washed with 2M hydrochloric acid
  3. customthe aqueous layer separated
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organics were dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6dbd6074b5504f07b9e49156f1ae7269
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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