Iodoethane → Ethyl 6-cyano-1-ethylindole-2-carboxylate

HRID 1532338ノート

反応式

HRID 1532338 の反応式
[H-].[Na+].I[CH2:4][CH3:5].[C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:14]2)=[CH:10][CH:9]=1)#[N:7]>CN(C)C=O.O>[C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]2[CH2:4][CH3:5])=[CH:10][CH:9]=1)#[N:7]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 4715002Ethyl 6-cyano-1H-indole-2-carboxylate

生成物 1

HCID 21251527Ethyl 6-cyano-1-ethylindole-2-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

In a 1 l flask, 23.5 g of ethyl 6-cyanoindole-2-carboxylate was dissolved in 300 ml of dimethylformamide, and 6.6 g of 60% NaH was slowly added thereto at 0° C. 17.6 ml of iodoethane was then added thereto at −10˜0° C. and the mixture was stirred for 2 hours at room temperature. The reaction solution was cooled and, after adding ice, diluted with water and then extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4 and then evaporated. The residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]. The fractions containing the desired product were combined and then evaporated to obtain 26.2 g of the title compound as a yellow solid.

後処理

  1. customat 0° C
  2. temperatureThe reaction solution was cooled
  3. additionafter adding ice
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]
  8. additionThe fractions containing the desired product
  9. customevaporated

出典と根拠

ORDレコード
ord-dc3e2711508f48df8b3988d06646cca6
出典データセット
uspto-grants-2001_03
特許番号
US06201006B1

反応ノート

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