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

HRID 1108264Notes

Reaction equation

HRID 1108264 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fc510df5a87d4528b3bce0508010f3a8
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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