Triethylamine → Methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl ester

HRID 2169246Notes

Reaction equation

HRID 2169246 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24].C(OCC)(=O)C>ClCCl.CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH2:14][O:15][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 86725895[1-(2,5-Dichlorophenyl)-cyclopentyl]-methanol

Product 1

HCID 86725896Methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl esterYield 78.12%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of [1-(2,5-dichlorophenyl)-cyclopentyl]-methanol (200) (23 g, 95.04 mmol) in dry dichloromethane (250 mL) was added dry triethylamine (26.42 mL, 190.083 mmol) slowly, then mesyl chloride (8.785 mL, 114.05 mmol) was added and the mixture was stirred for 16 h at room temperature. Silica thin layer chromatography was performed (10% ethyl acetate in hexane, Rf=0.5) After completion of the reaction, the mixture was diluted with water, and extracted with dichloromethane. The combined organic layer was washed with brine, and dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified using normal silica gel (100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get pure methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl ester (201) (24 g, 78.12%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-1f578c32a625430aa7c88c18d9b8da2b
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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