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

HRID 1841696ノート

反応式

HRID 1841696 の反応式
[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].[K].C(=O)([O-])[O-].I[CH2:19][CH:20]([CH3:23])[CH2:21][CH3:22]>CC(C)=O>[CH3:19][CH:20]([CH2:21][CH3:22])[CH2:23][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]

参加物

6

反応物 4

HCID 19660Carbonate IonHCID 1414791-Iodo-2-methylbutaneHCID 261887Methyl 4-nitro-1h-pyrrole-2-carboxylateHCID 5462222Potassium

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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 vacuo, 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) δ 8.30 (d, 1H, J=2.0 Hz), 7.33 (d, 1H, J=1.9 Hz), 4.15 (d, 2H, J=7.4 Hz), 3.77 (s, 3H), 2.03 (m, 1H, J=3.1 Hz), 0.80 (d, 6H, J=6.7 Hz); 13C NMR (DMSO-d6) δ 160.30, 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.

後処理

  1. temperaturerefluxed for 10 hours
  2. concentrationconcentrated in vacuo
  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

出典と根拠

ORDレコード
ord-835d3c7625384a36814879dc04762286
出典データセット
uspto-grants-2004_01
特許番号
US06683189B1

反応ノート

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