Pyridine → Cyclopentyl methanesulfonate

HRID 1684324Notes

Reaction equation

HRID 1684324 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].N1C=CC=CC=1>CCOCC>[CH3:7][S:8]([O:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7298CyclopentanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 13066113Cyclopentyl methanesulfonateYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round-bottomed flask (1,000 cc) equipped with a mechanical stirrer was charged with cyclopentyl alcohol (51.2 g, 0.595 mol) and methanesulfonyl chloride (75.1 g, 0.656 mol), followed by the addition of pyridine (200 mL) under ice cooling to form a solution. The solution was stirred for 6 h as it was warmed gradually to room temperature. After completion of the reaction, the reaction mixture was poured into ice water (300 mL) and extraction was conducted with ether (200 mL×3). The organic layers were washed with water, 1N HCl and saturated brine and dried with anhydrous magnesium sulfate. Distilling off the solvent under vacuum gave cyclopentyl methanesulfonate as a colorless oil (75.2 g, 0.458 mol; yield=77.0%). 1H-NMR(CDCl3,TMS,ppm): δ1.54-2.03(8H,m), 3.01(3H,s), 5.19(1H,m).

Workup

  1. customA round-bottomed flask (1,000 cc) equipped with a mechanical stirrer
  2. customto form a solution
  3. customAfter completion of the reaction
  4. washThe organic layers were washed with water, 1N HCl and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationDistilling off the solvent under vacuum

Sources & evidence

ORD record
ord-7da833be7ed441b3896e9d9af9719a9e
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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