Ethanol → Methyl indole-6-carboxylate

HRID 1242125

反応式

HRID 1242125 の反応式
O1CCCC1.C(O)C.CN(C)/[CH:11]=[CH:12]/[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:23]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:20][O:19][C:17]([C:16]1[CH:15]=[C:14]2[C:13]([CH:12]=[CH:11][NH:23]2)=[CH:22][CH:21]=1)=[O:18]

参加物

6

反応物 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

生成物 1

HCID 639844Methyl indole-6-carboxylate収率 39.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a mixed solvent of tetrahydrofuran (30 ml), ethanol (30 ml) and water (100 ml), added are methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (10.0 g) and sodium hydrosulfite (104.5 g), and stirred at 70° C. for 1 hours. After this is cooled to room temperature, a saturated saline solution is added thereto. Then, this is extracted with chloroform. The organic layer is dried, and the solvent is evaporated away. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1) to obtain 6-methoxycarbonylindole (2.79 g).

後処理

  1. temperatureAfter this is cooled to room temperature
  2. additiona saturated saline solution is added
  3. extractionThen, this is extracted with chloroform
  4. customThe organic layer is dried
  5. customthe solvent is evaporated away
  6. customThe resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1)

出典と根拠

ORDレコード
ord-c315ac36537f4e9db6abb6977f887501
出典データセット
uspto-grants-2006_10
特許番号
US07115647B2

関連ノート

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