Triethylamine → (1-Phenylcyclopentyl)methyl methanesulfonate

HRID 2169153Notes

Reaction equation

HRID 2169153 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.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[C:1]1([C:7]2([CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])[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 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-phenyl-cyclopentyl)-methanol (23-01) (9.1 gm, 51.70 mmol) in dichloromethane (100 mL) was added triethyl amine (14.4 mL, 104.96 mmol) followed by methanesulfonyl chloride (5.09 ml, 62.045 mmol) at cooling condition, it was stirred at room temperature for 16 h. After completion of the reaction, the mixture was diluted with dichloromethane, washed with water, sodium bicarbonate solution and brine. The separated organic part was dried over sodium sulfate and evaporated under reduced pressure to get methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (24-01) (13 g) as a crude product.

Workup

  1. temperatureat cooling condition, it
  2. customAfter completion of the reaction
  3. washwashed with water, sodium bicarbonate solution and brine
  4. dry with materialThe separated organic part was dried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-208b84d3125a41c18f81e89ac8638405
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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