Methanesulfonyl chloride → (1-Phenylcyclopentyl)methyl methanesulfonate

HRID 1409553Notes

Reaction equation

HRID 1409553 reaction equation
[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[C:1]1([C:7]2([CH2:12][O:13][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 123544(1-Phenylcyclopentyl)methanol

Product 1

HCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonateYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-phenyl-cyclopentyl)-methanol (11.5 g, 64.34 mmol) in DCM (100 ml) was added TEA (17.5 ml, 130.68 mmol) and followed by methanesulfonyl chloride (MsCl) (8.9 g, 78.4 mmol) was added drop wise at 0° C. and the reaction mixture was stirred at RT for 16 h. After completion of the reaction, it was quenched with water and concentrated. Then the crude product was dissolved in DCM, extracted with DCM and the organic layer was washed with water, and brine and then dried over Na2SO4. The combined organic layer was concentrated to get crude methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (10 g, crude) as a white solid.

Workup

  1. additionwas added drop wise at 0° C.
  2. customAfter completion of the reaction, it
  3. customwas quenched with water
  4. concentrationconcentrated
  5. dissolutionThen the crude product was dissolved in DCM
  6. extractionextracted with DCM
  7. washthe organic layer was washed with water, and brine
  8. dry with materialdried over Na2SO4
  9. concentrationThe combined organic layer was concentrated

Sources & evidence

ORD record
ord-087fa2896d7a4b46841ac6d5ff349e6f
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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