Triethylamine → Methanesulfonic acid 1-(4-chlorophenyl)-cyclopentylmethyl ester

HRID 2169356Notes

Reaction equation

HRID 2169356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:13][O:14][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27240171-(p-Chlorophenyl)cyclopentanemethanol

Product 1

HCID 86725805Methanesulfonic acid 1-(4-chlorophenyl)-cyclopentylmethyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(4-chlorophenyl)-cyclopentyl]-methanol (319) (12 g, 56.95 mmol) in dichloromethane (110 mL) was added triethyl amine (16 mL, 113.90 mmol) followed by mesyl chloride (5.3 mL, 68.34 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 h, diluted with dichloromethane (50 mL) and washed with water (100 mL), saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL). The organic part was dried, concentrated and purified by CombiFlash column (eluted at 10-20% ethyl acetate in hexane) to get methanesulfonic acid 1-(4-chlorophenyl)-cyclopentylmethyl ester (320) (14 g, 85%) as a light yellow crystalline solid.

Workup

  1. washwashed with water (100 mL), saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL)
  2. customThe organic part was dried
  3. concentrationconcentrated
  4. custompurified by CombiFlash column (eluted at 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d1061fd77ab04bb89eac3340b8fe5469
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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