Methyl iodide → ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1508496노트

반응식

HRID 1508496 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:14]I>C1COCC1>[CH3:14][N:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

생성물 1

HCID 14296950ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-methyl-2-pyrrolecarboxylic acid ethyl ester (100 mg, 0.653 mmol) in THF (2.5 mL), was added NaH (31.3 mg, 0.783 mmol). The mixture was stirred for 10 min and then MeI (0.061 mL, 0.979 mmol) was added dropwise. The resulting mixture was stirred overnight. The reaction was quenched with sat. NH4Cl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate. 1H NMR (500 MHz, CDCl3): δ 6.77 (s, 1H); 6.58 (s, 1H); 4.28 (q, J=7.1 Hz, 2H); 3.88 (s, 3H); 2.08 (s, 3H); 1.35 (t, J=7.1 Hz, 3H).

후처리

  1. stirringThe resulting mixture was stirred overnight
  2. customThe reaction was quenched with sat. NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

출처 및 근거

ORD 기록
ord-b04b0124c109414c887776ac9ebb7677
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221834B2

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