Pyrrole → N-Triisopropylsilylpyrrole

HRID 398823Notes

Reaction equation

HRID 398823 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH:11]([Si:14](Cl)([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>C1COCC1.CCCCCC.C(OCC)C>[CH:11]([Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:13])[CH3:12]

Participants

7

Reactant 3

HCID 8027PyrroleHCID 139400Triisopropylsilyl chlorideHCID 178418339Butyllithium

Product 1

HCID 145136N-TriisopropylsilylpyrroleYield 91.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of pyrrole (33.54 g) in THF (700 ml) at -78° C. under nitrogen was added a solution of 2.5M n-butyl lithium(200 ml) in hexane. After one hour triisopropylsilyl chloride (98 g) was added. After 24 hours the reaction was diluted with diethyl ether, washed with water, dried over sodium sulfate, filtered and evaporated to a tan oil which was distilled at 115°-119° C. (0.2 mm Hg) to give 102.6 g of a colorless mobile liquid. 1H NMR is consistent with proposed structure.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to a tan oil which
  5. distillationwas distilled at 115°-119° C. (0.2 mm Hg)

Sources & evidence

ORD record
ord-1d6f69356dde4a7fb32ecd0612116bac
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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