Pyrrole → N-Triisopropylsilylpyrrole

HRID 389003Notes

Reaction equation

HRID 389003 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[H][H].[CH:10]([Si:13](Cl)([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])([CH3:12])[CH3:11]>CN(C=O)C>[CH:10]([Si:13]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 8027PyrroleHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 145136N-TriisopropylsilylpyrroleYield 30.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Pyrrole (1.0 mL, 0.96 g, 15 mmol) was added dropwise at 0° C. to a stirred suspension of sodium hydride (0.758 g of 50% dispersion in mineral oil, 16 mmol) in anhydrous DMF (20 mL). When hydrogen evolution (foaming) had ceased, triisopropylsilyl chloride (3.1 mL, 2.8 g, 15 mmol) was added dropwise and stirring at 0° C. was then continued for 0.75 h. The reaction mixture was partitioned between ether and water, and the ether phase was washed with water, dried oversodium sulfate, and evaporated in vacuum. Purification by column chromatography on silica gel (hexane/ethyl acetate=10:1) gave an oil (1.01 g, 30.2% yield); 1H NMR (CDCl3) δ 1.09 (d, 18 H, Me), 1.45 (sept, 3 H, CH), 6.31 (t, 2H, H-3.4), 6.80 (t, 2H, H-2.5). MS (M+H) m/z 224.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. washthe ether phase was washed with water
  3. dry with materialdried oversodium sulfate
  4. customevaporated in vacuum
  5. customPurification by column chromatography on silica gel (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-8b6c154a19c94d9b8460576a6dfe98f2
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Reaction notes

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