Ethanol → Methyl indole-6-carboxylate

HRID 1242125

반응식

HRID 1242125 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 639844Methyl indole-6-carboxylate수율 39.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c315ac36537f4e9db6abb6977f887501
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115647B2

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