Sodium hydride → 2-Methoxycarbonyl-1-triisopropylsilylpyrrole

HRID 1108263ノート

反応式

HRID 1108263 の反応式
I[C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.[H-].[Na+].N1C=CC=C1C(OC)=O.C([Si](Cl)(C(C)C)C(C)C)(C)C>CCCCC.O1CCCC1>[CH3:10][O:9][C:7]([C:5]1[N:4]([Si:11]([CH:12]([CH3:14])[CH3:13])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:3]=[CH:2][CH:6]=1)=[O:8]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylateHCID 139400Triisopropylsilyl chlorideHCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole

生成物 1

HCID 187846382-Methoxycarbonyl-1-triisopropylsilylpyrrole収率 73%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole starting material can be prepared as follows. Sodium hydride (80% dispersion; 660 mg, 22 mmol) was washed with pentane and suspended in tetrahydrofuran (20 mL). A solution of methyl pyrrole-2-carboxylate (1.251 g, 10 mmol) in tetrahydrofuran (10 mL) was added and the mixture stirred at room temperature. When gas evolution ceased, triisopropylsilyl chloride (1.928 mg, 10 mmol) was added dropwise, and the mixture was stirred for 1 hour, heated at reflux overnight, and partitioned between ether and water. The ethereal layer was dried (magnesium sulfate) and concentrated in vacuo. The residue was purified by chromatography using hexanes:ethyl acetate (8:1) to yield 2-methoxycarbonyl-1-triisopropylsilylpyrrole as an oil (2.05 g, 73%): 1H NMR (CDCl3) δ 7.12 (m, 2H), 6.26 (m, 1H), 3.78 (m, 3H), 1.76 (sept, 3H, J=7.6 Hz), 1.04 (d, 18 H, J=7.6 Hz).

後処理

  1. stirringthe mixture was stirred for 1 hour
  2. temperatureheated
  3. temperatureat reflux overnight
  4. custompartitioned between ether and water
  5. dry with materialThe ethereal layer was dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-d16158c41ba7410d90c0876df7218622
出典データセット
uspto-grants-2000_05
特許番号
US06066639

反応ノート

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