Methanol → diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylate

HRID 1748264ノート

反応式

HRID 1748264 の反応式
CO.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[C:22](#[N:25])[CH:23]=[CH2:24].O>O1CCOCC1>[C:22]([CH2:23][CH2:24][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:25]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 7855AcrylonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2 回

生成物 1

HCID 67235491diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylate収率 96%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
55 °C

実験手順

A 40% solution of Triton B in methanol (0.50 mL, 1.1 mmol) is added to a suspension of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 2.6 g, 10.0 mmol) and acrylonitrile (2.2 mL, 33.4 mmol) in 1,4-dioxane (25 mL). The reaction mixture is warmed to 55° C. for 30 min and then it is stirred at room temperature for 18 h. Water (30 mL) is added and the mixture is extracted with EtOAc. The organic layer is washed with water, brine, dried (Na2SO4) and concentrated to afford the title crude compound (3.0 g, 96%) as a yellow solid which is used in the next step without purification.

後処理

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-10e21f41970548efb6dba657d9aa025b
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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