Pyrrole → N-Triisopropylsilylpyrrole

HRID 256560Notes

Reaction equation

HRID 256560 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13]>CCOCC.C1OCCOCCOCCOCCOCCOC1>[CH:12]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 8027PyrroleHCID 139400Triisopropylsilyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 145136N-TriisopropylsilylpyrroleYield 86%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 3283Diethyl EtherSolvent

Procedure

Pyrrole (2.9 ml, 42 mmol) was added dropwise with stirring at room temperature to a suspension of potassium tert-butoxide (4.66 g, 42 mmol) and 18-crown-6 (0.2 g, 0.76 mmol) in ether (300 ml). After 1 hour tri-isopropylsilyl chloride (8.0 g, 42 mmol) was added dropwise, and then the reaction mixture was stirred for 16 hours, and filtered. The residue was washed with ether and the combined filtrate and washings were washed with brine, then dried and concentrated to give N-tri-isopropylsilylpyrrole (8.0 g, 86% yield) as a clear oil, 1H nmr: delta 1.04 (18H, d), 1.38 (3H, m), 6.22 (2H, m), 6.72 (2H, m) ppm.

Workup

  1. filtrationfiltered
  2. washThe residue was washed with ether
  3. washthe combined filtrate and washings were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4259472c90d64fd08f48ef74c18a68d2
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Reaction notes

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