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

HRID 1108264ノート

反応式

HRID 1108264 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 187846613-Iodo-5-methoxycarbonyl-1-triisopropylsilylpyrrole収率 88.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fc510df5a87d4528b3bce0508010f3a8
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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