Sodium hydride → HCID 70032910、化合物

HRID 434020

反応式

HRID 434020 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH2:21]1[O:25][C:24]2[CH:26]=[C:27]([Cl:32])[C:28]([CH2:30]Cl)=[CH:29][C:23]=2[O:22]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:30][C:28]2[C:27]([Cl:32])=[CH:26][C:24]3[O:25][CH2:21][O:22][C:23]=3[CH:29]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 901136-Chloropiperonyl chlorideHCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

生成物 1

HCID 70032910HCID 70032910、化合物収率 43%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of NaH (60% suspension in mineral oil, 0.24 g, 6.12 mmol) and DMF (20 mL) was added 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol), from Example 1(d). After stirring at room temperature for 1 h, 6-chloropiperonyl chloride (0.84 g, 4.08 mmol) was added followed by the addition of tetrabutyl ammonium iodide (0.15 g, 0.41 mmol). The reaction was stirred at room temperature for 18 h. When the reaction was complete as indicated by TLC, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed in vacuo and the resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes) to yield the desired product as an oil (0.72 g, 43%). LC/MS (ES+) m/e 414.0 [M+H]+.

後処理

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b1232f5cd63a4771b76d4c4fa67413d4
出典データセット
uspto-grants-2003_12
特許番号
US06670388B1

関連ノート

読み込み中…