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

HRID 2169269노트

반응식

HRID 2169269 반응식
[Br: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.CCN(CC)CC.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>ClCCl>[Br: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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67480063[1-(4-Bromophenyl)cyclopentyl]methanol

생성물 1

HCID 86725919Methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred of [1-(4-bromophenyl)-cyclopentyl]-methanol (226) (47.0 g, 184.19 mmol) in dichloromethane (300 mL) was added Et3N (51.3 mL, 368.39 mmol) followed by dropwise addition of mesyl chloride (17.1 mL, 221.03 mmol) at 0° C., and the reaction mixture stirred at room temperature for 1 h. The reaction was quenched by the addition of water, extracted with dichloromethane, washed with water, dried over Na2SO4 and concentrated. The crude product was purified by 100-200 silica column chromatography using 5% ethyl acetate in hexane as the eluent to give methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester (227) (52.8 g, 86%) as a white solid.

후처리

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by 100-200 silica column chromatography

출처 및 근거

ORD 기록
ord-206e3a4bd27c492f9dd6556c7b128cf9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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