Ethyl Acetate → [4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

HRID 1644716

反応式

HRID 1644716 の反応式
C(O[C:4](=O)[CH2:5][CH2:6]C=O)C.C([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=O.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[O:38]1CCOCC1>[Au](Br)(Br)Br>[CH2:36]([O:35][C:32](=[O:34])[CH2:33][C:5]1[CH:6]=[C:18]([C:19](=[O:38])[C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:27])(=[O:28])[N:29]([CH3:30])[CH3:31])=[CH:22][CH:21]=2)[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1)[CH3:37]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 82395Ethyl 4-oxobutanoateHCID 593508554-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide

生成物 1

HCID 59350849[4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester収率 29%

試薬・触媒・溶媒 1

HCID 82525Gold tribromide触媒

反応条件

温度
100 °C

実験手順

A suspension of gold(III) bromide (38 mg, 0.087 mmol), 4-oxo-butyric acid ethyl ester (377 mg, 2.9 mmol) and 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide (454 mg, 1.45 mmol) in anhydrous dioxane (10 mL) was heated at 100° C. for 4 hours. After being cooled to room temperature, the mixture was treated with ethyl acetate, and then washed with water. The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 25-60% ethyl acetate in hexane) gave [4-(4-dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (180 mg, 29%). MS (ESI+) cald. for C23H23NO5S [(M+H)+] 425, obsd. 426.

後処理

  1. temperatureAfter being cooled to room temperature
  2. washwashed with water
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5b350a69c57e4ada870ac98732ece1a2
出典データセット
uspto-grants-2012_02
特許番号
US08124629B2

関連ノート

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