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Water → 5-Methoxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole

HRID 2225884
ノート
印刷プレビュー

反応式

HRID 2225884 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][O:13][CH3:14])=[C:5]2[C:15]([O:17][CH3:18])=[O:16].[H-].[Na+].[CH3:21]I.O>CN(C)C=O>[CH3:21][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][O:13][CH3:14])=[C:5]2[C:15]([O:17][CH3:18])=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10198835Methyl 5-hydroxy-2-(methoxymethyl)-1-methyl-1H-indole-3-carboxylate

生成物 1

HCID 106591965-Methoxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole収率 89.6%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
50 °C

実験手順

14.9 g of 5-hydroxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole (59.8 mmol) obtained in Example 1 was dissolved in 150 ml of anhydrous dimethylformamide, and the solution was stirred in a stream of nitrogen under ice cooling. To this were added 2.63 g (65.8 mmol) of sodium hydride (60% oil dispersion) and 4.1 ml (65.9 mmol) of methyl iodide in that order. After 2 hours of heating at 50° C., the resulting reaction mixture was cooled down, mixed with water and then extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off and the solvent was distilled off under reduced pressure, the resulting residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate, 3:1) to obtain 14.1 g of the title compound with a yield of 89%.

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas cooled down
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter anhydrous magnesium sulfate was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-eb0537d5274c4574b6c1c7f9c71f8041
出典データセット
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05344938

反応ノート

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