Methyl iodide → Ethyl 5-chloro-1-methyl-1H-indole-2-carboxylate

HRID 2164099노트

반응식

HRID 2164099 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2.[CH3:18]I>CN(C)P(=O)(N(C)C)N(C)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:18])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 78518Ethyl 5-chloroindole-2-carboxylate

생성물 1

HCID 3911003Ethyl 5-chloro-1-methyl-1H-indole-2-carboxylate수율 85%

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

실험 절차

8.7 gm (0.2 mol) of a 55% dispersion of sodium hydride in oil were added over a period of 15 minutes at a temperature of 0° C. and in a nitrogen atmosphere to a solution of 40.0 gm (0.18 mol) of ethyl 5-chloro-indole-2-carboxylate in 150 ml of hexamethyl-phosphoric acid triamide. After stirring the resulting mixture for 2.5 hours at room temperature, 35.5 gm (0.25mol) of methyl iodide were added dropwise, while cooling. After stirring overnight, 1200 ml of ice water were added to the mixture, while externally cooling on an ice bath. The aqueous mixture was then extracted 5 times with 150 ml of ether each. The combined ether extracts were washed with water 5 times, dried over magnesium sulfate, and evaporated in vacuo. The raw product was then recrystallized from petroleum ether, yielding 35.8 gm (85% of theory) of ethyl 5-chloro-1-methyl-indole-2-carboxylate. M.p.: 81.5°-82° C.

후처리

  1. temperaturewhile cooling
  2. stirringAfter stirring overnight
  3. temperaturewhile externally cooling on an ice bath
  4. extractionThe aqueous mixture was then extracted 5 times with 150 ml of ether each
  5. washThe combined ether extracts were washed with water 5 times
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe raw product was then recrystallized from petroleum ether

출처 및 근거

ORD 기록
ord-aeb2a42f51004d7a96f1f4bb6c00d7b0
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04137313

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