Triethylamine → (1-Phenylcyclopentyl)methyl methanesulfonate

HRID 2169310Notes

Reaction equation

HRID 2169310 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.C(N(CC)CC)C.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>ClCCl>[C:1]1([C:7]2([CH2:12][O:13][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123544(1-Phenylcyclopentyl)methanol

Product 1

HCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonateYield 83.16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1-phenyl-cyclopentyl)-methanol] (278) (10 g, 56.73 mmol) in dichloromethane (110 mL) was added triethyl amine (16 mL, 113.47 mmol) followed by mesyl chloride (5.3 mL, 68.08 mmol) at 0° C. Stirring was continued at room temperature for 16 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (50 mL) and washed with water (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL). The separated organic fraction was dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to get methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (279) (12 g, 83.16%) as a yellow semi-solid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL)
  3. customThe separated organic fraction was dried
  4. concentrationconcentrated
  5. customThe crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4ba4289f23ba49bab0e20bca91a69c26
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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