N-Iodosuccinimide → 3-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole

HRID 1108264노트

반응식

HRID 1108264 반응식
[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[N:14]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1)=[O:12]>O1CCCC1>[I:1][C:16]1[CH:17]=[C:13]([C:11]([O:10][CH3:9])=[O:12])[N:14]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:25]([CH3:27])[CH3:26])[CH:15]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 187846382-Methoxycarbonyl-1-triisopropylsilylpyrrole

생성물 1

HCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole수율 88.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-Iodosuccinimide (653 mg, 2.9 mmol) was added to a stirred solution of 2-methoxycarbonyl-1-triisopropylsilylpyrrole (815 g, 2.9 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred at room temperature for two days. The solvent was then removed in vacuo and the oily residue suspended in hexanes (50 mL) with vigorous stirring. The insoluble solid was removed by filtration and the filtrate concentrated in vacuo. Purification of the residue by column chromatography using hexanes gave 3-iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole (1.044 g, 88%) as a white crystalline solid, mp 81-83° C.: 1H NMR (CDCl3) δ 7.18 (d, 1H, J=1 5 Hz), 7.09 (d, 1H, J=1.5 Hz), 379 (s, 3H), 1.74 (sept, 3H, J=7.6 Hz), 1.11 (d, 18H, J=7.6 Hz).

후처리

  1. customThe solvent was then removed in vacuo
  2. customThe insoluble solid was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by column chromatography

출처 및 근거

ORD 기록
ord-fc510df5a87d4528b3bce0508010f3a8
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066639

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