Potassium Carbonate → Methyl N-2-methyl-butyl-4-nitropyrrole-2-carboxylate

HRID 1265493노트

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HRID 1265493 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH:21]([CH3:24])[CH2:22][CH3:23]>CC(C)=O>[CH3:20][CH:21]([CH2:22][CH3:23])[CH2:24][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]1[C:9]([O:11][CH3:12])=[O:10]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1414791-Iodo-2-methylbutaneHCID 261887Methyl 4-nitro-1h-pyrrole-2-carboxylate

생성물 1

HCID 23446390Methyl N-2-methyl-butyl-4-nitropyrrole-2-carboxylate수율 70%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Methyl 3-nitropyrrole-2-carboxylate (22) (2.7 g, 15.9 mmol), potassium carbonate (6.5 g), and iodo-2-methylbutane (5.2 ml) were dissolved in 100 ml of acetone and refluxed for 10 hours. The reaction mixture was then cooled to room temperature, concentrated in vacua, partitioned between 200 ml of dichloromethane and 200 ml of water and extracted with dichloromethane (2×200 ml). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The resulting yellow oil was purified by flash chromatography to provide the substituted nitro pyrrole 23 (2.5 g, 70% yield). 1H NMR (DMSO-d6) δ8.30 (d, 1 H, J=2.0 Hz), 7.33 (d, 1 H, J=1.9 Hz), 4.15 (d, 2 H, J=7.4 Hz), 3.77 (s. 3H), 2.03 (m, 1 H, J=3.1 Hz), 0.80 (d. 6 H, J=6.7 Hz); 13C NMR (DMSO-d6) δ160.30, 134.79, 129.80, 122.40, 112.76, 105.00, 56.63, 52.41, 29.72, 19.73; FABMS, 226.096 calcd, 226.095 found.

후처리

  1. temperaturerefluxed for 10 hours
  2. concentrationconcentrated in vacua
  3. custompartitioned between 200 ml of dichloromethane and 200 ml of water
  4. extractionextracted with dichloromethane (2×200 ml)
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe resulting yellow oil was purified by flash chromatography

출처 및 근거

ORD 기록
ord-d59f97753ab347eaaac8cb663981742e
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545162B1

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