Water → 1,6-Dimethyl-1H-indole-3-carbaldehyde

HRID 442744

反応式

HRID 442744 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[CH3:15][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 47779026-Methylindole-3-carboxaldehyde

生成物 1

HCID 225937461,6-Dimethyl-1H-indole-3-carbaldehyde収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of the known 6-methyl-1H-indole-3-carboxaldehyde (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97%).

後処理

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with ethylacetate (EtOAc) (200 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-56cb28cf919340c083e1a725acc2a2fc
出典データセット
uspto-grants-1999_04
特許番号
US05891901

関連ノート

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