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

HRID 2169269ノート

反応式

HRID 2169269 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-206e3a4bd27c492f9dd6556c7b128cf9
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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