2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Formyl-5-methoxy-3-methoxycarbonyl-1-methylindole

HRID 2225886ノート

反応式

HRID 2225886 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([CH2:13][O:14]C)=[C:6]2[C:16]([O:18][CH3:19])=[O:17].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH:13]([C:7]1[N:8]([CH3:12])[C:9]2[C:5]([C:6]=1[C:16]([O:18][CH3:19])=[O:17])=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:14]

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 106591965-Methoxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole

生成物 1

HCID 107529932-Formyl-5-methoxy-3-methoxycarbonyl-1-methylindole収率 72%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5.0 g (19.0 mmol) of 5-methoxy-3-methoxycarbonyl-2-methoxymethyl -1-methylindole obtained in Example 2 or 4 was dissolved in 200 ml of anhydrous toluene, followed by the addition of 4.94 g (20.9 mmol) of DDQ and subsequent 2 hours of heating under reflux. After cooling the reaction mixture and removing impurities by filtration, the organic 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: hexaneethyl acetate, 3:1) to obtain 3.38 g of the title compound with a yield of 72%.

後処理

  1. temperatureof heating
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction mixture
  4. customremoving impurities
  5. filtrationby filtration
  6. washthe organic layer was washed with water and saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter anhydrous magnesium sulfate was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexaneethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-7e54d5054b094e548ab2d0465c096eb5
出典データセット
uspto-grants-1994_09
特許番号
US05344938

反応ノート

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