Methyl iodide → Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

HRID 515864

반응식

HRID 515864 반응식
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12]I.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][N:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]1[CH3:1]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

생성물 1

HCID 12211514Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 10 g of ethyl 2-methyl-1H-pyrrole-3-carboxylate (65.3 mmol) and 8.95 mL (130.6 mmol) of methyl iodide in 70 mL of dimethylformamide placed at 0° C. there are added, in three portions, 2.61 g (65.3 mmol) of sodium hydride (NaH) 60% . The batch is then stirred at 0° C. for 1 hour. Then, the reaction mixture is hydrolysed by the addition of 420 mL of ice-cold water. The reaction mixture is then diluted with ethyl acetate, successively washed with 0.1M aqueous hydrochloric acid (HCl) solution, saturated aqueous LiCl solution and then brine. The organic phase is then dried over MgSO4, filtered, concentrated to dryness and purified by chromatography over silica gel (petroleum ether/AcOEt gradient).

후처리

  1. customplaced at 0° C.
  2. washsuccessively washed with 0.1M aqueous hydrochloric acid (HCl) solution, saturated aqueous LiCl solution
  3. dry with materialThe organic phase is then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. custompurified by chromatography over silica gel (petroleum ether/AcOEt gradient)

출처 및 근거

ORD 기록
ord-527b8670a95e40e989aab6cfe6fb9720
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108983B2

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