Dimethylformamide → ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

HRID 420144ノート

反応式

HRID 420144 の反応式
O=P(Cl)(Cl)Cl.[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[CH:11]=[CH:10]2)[CH2:8][CH2:7]1.CN([CH:28]=[O:29])C>CCOC(C)=O.[OH-].[Na+]>[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[C:11]([CH:28]=[O:29])=[CH:10]2)[CH2:7][CH2:8]1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate

生成物 1

HCID 86621575ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

1.28 ml of POCl3 was added dropwise to a solution of 3.24 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate in 30 ml of DMF and the mixture was stirred at 0° C. for 2 hrs. The mixture was diluted with EtOAc and 25 ml of 1N NaOH was added. Then the mixture was made basic using saturated NaHCO3aq. The mixture was extracted with EtOAc and the extract was washed with water and saturated brine, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system) to give 2.4 g of ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate.

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system)

出典と根拠

ORDレコード
ord-ce40d6d2c83442999f30661b6b7ba9a4
出典データセット
uspto-grants-2012_01
特許番号
US08093389B2

反応ノート

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