Sodium hydride → 2-Methoxycarbonyl-1-triisopropylsilylpyrrole

HRID 1108263노트

반응식

HRID 1108263 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 187846382-Methoxycarbonyl-1-triisopropylsilylpyrrole수율 73%

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d16158c41ba7410d90c0876df7218622
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066639

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