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m-Chloroperbenzoic acid → 3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester

HRID 1367473
ノート
印刷プレビュー

反応式

HRID 1367473 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7](SC2C=CC=CC=2Cl)[CH2:6]1)=[O:4].[CH:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20](C(OO)=O)[CH:19]=1.[S:29](=[O:32])(O)[O-:30].[Na+]>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([S:29]([C:23]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[Cl:24])(=[O:32])=[O:30])[CH2:6]1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 669185443-(2-Chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester

生成物 1

HCID 669185503-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 3-(2-chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester (0.24 g, 1.0 eq) in dichloromethane (10 mL) was treated at 0° C. with a solution of MCPBA (1.1 g, 5.0 eq) in dichloromethane (7 mL), which was added dropwise. The mixture was stirred at 0° C. for 3 h, then treated with 20% sodium bisulfite and stirred at RT for 15 min. The mixture was filtered, washing with chloroform. The organic phase was washed with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient, yielding the title compound as a colorless oil (0.25 g, 90%). MS (ESI): m/z=303.2 [M+H]+.

後処理

  1. additionwas added dropwise
  2. stirringstirred at RT for 15 min
  3. filtrationThe mixture was filtered
  4. washwashing with chloroform
  5. washThe organic phase was washed with saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient

出典と根拠

ORDレコード
ord-bc2ad3f332d74e68afdee6e6971481d1
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07893099B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート