Benzyl Bromide → 1h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-

HRID 3386ノート

反応式

HRID 3386 の反応式
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].CCCCCC.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[C:24]1([CH2:23][N:4]2[C:5]3[C:10](=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[CH2:1][CH3:2])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 130479942-ethyl-4-nitro-1H-indole

生成物 1

HCID 105407101h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

2-Ethyl-4-nitro-1H-indole (4.75 g, 25 mmol) was added to a mixture of 1.0 g (25 mmol) of 60% NaH/mineral oil (washed with hexane before adding DMF) in 40 ml DMF. After 45 minutes, 3.0 ml (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for four hours, diluted with water, and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane to give 6.36 g (91%) of 1-Phenylmethyl-2-ethyl-4-nitro-1H-indole as an oil.

後処理

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane

出典と根拠

ORDレコード
ord-bbf8230acb4c4efbbe2e5b95721c489b
出典データセット
uspto-grants-1998_03
特許番号
US05733923

反応ノート

読み込み中…