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

HRID 420140ノート

反応式

HRID 420140 の反応式
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([OH:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[C:19]([O-])([O-])=O.[K+].[K+].CN(C=O)C.CI>CCOC(C)=O>[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:18][CH3:19])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

生成物 1

HCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate収率 98.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a stirred suspension of 14.56 g of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate and 16.2 g of K2CO3 and 220 ml of DMF was added 7.48 ml of MeI and the mixture was stirred at 60° C. for 3 hrs. The mixture was allowed to cool, diluted with EtOAc, washed with water and saturated brine successively, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (n-hexane-EtOAc) to afford 15.15 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate as a pale yellow oil.

後処理

  1. temperatureto cool
  2. washwashed with water and saturated brine successively
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified on SiO2 column chromatography (n-hexane-EtOAc)

出典と根拠

ORDレコード
ord-0eb400ffa6964be08a89773913045090
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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