Triethylamine → Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester

HRID 2169280노트

반응식

HRID 2169280 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCN(CC)CC.[S:25](Cl)([CH3:28])(=[O:27])=[O:26]>ClCCl>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][O:15][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86725928[1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-methanol

생성물 1

HCID 86725929Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester수율 70.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred of 1-(4-trifluoromethyl-phenyl)-cyclopentyl]-methanol (239) (15 g, 61.47 mmol) in dichloromethane (200 mL) was added Et3N (17.1 mL, 123 mmol) followed by mesyl chloride (5.7 mL, 73.77 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h. After completion, the reaction was quenched by the addition of water. The reaction mixture was diluted with dichloromethane. The organic part was washed with water, separated, dried over Na2SO4 and finally concentrated. The crude product was purified by 100-200 silica column chromatography using 10% ethyl acetate in hexane as the eluent to give methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester (240) (14 g, 70.6%) as a white solid.

후처리

  1. customAfter completion, the reaction was quenched by the addition of water
  2. additionThe reaction mixture was diluted with dichloromethane
  3. washThe organic part was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationfinally concentrated
  7. customThe crude product was purified by 100-200 silica column chromatography

출처 및 근거

ORD 기록
ord-114586647b7d4f008c393d4051bc9cd1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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