Cyclopentanol → Cyclopentyl methanesulfonate

HRID 1095186Notes

Reaction equation

HRID 1095186 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].C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 13066113Cyclopentyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of cyclopentanol (Aldrich, 2.58 g, 30 mmol) in methylene chloride (150 mL) at 0° C., Methane sulfonyl chloride (2.55 mL, 33 mmol) and triethyl amine (5.23 mL, 37.5 mmol) were added slowly and the mixture was stirred for 1.5 hrs. The reaction was quenched with water and the mixture was washed with 0.5 N HCl and brine solution. The organic layer was dried with sodium sulfate. Removal of solvent gave a colorless oil. 5.1 g.

Workup

  1. customThe reaction was quenched with water
  2. washthe mixture was washed with 0.5 N HCl and brine solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customRemoval of solvent
  5. customgave a colorless oil

Sources & evidence

ORD record
ord-f73f2565f28a4a4f94bd1c314a9dcf61
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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