Chlorotrimethylsilane → 4-(3-Formyl-n-propyl)-1-trimethylsilylimidazole

HRID 477969Notes

Reaction equation

HRID 477969 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1)=O)C.[H-].[Na+].[CH3:16][Si:17](Cl)([CH3:19])[CH3:18]>O1CCCC1>[CH:4]([CH2:6][CH2:7][CH2:8][C:9]1[N:10]=[CH:11][N:12]([Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:13]=1)=[O:3]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 178471275HCID 178471275, compound

Product 1

HCID 199304284-(3-Formyl-n-propyl)-1-trimethylsilylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.82 g of 4-(3-ethoxycarbonylpropyl)-1H-imidazole in 30 ml of tetrahydrofuran under nitrogen is treated with 0.5 g of sodium hydride (50% oil dispersion) at 0° for 30 min and 1.45 ml of trimethylsilyl chloride at 0° for 3 h. The reaction mixture is washed with cold 0.5N sodium bicarbonate solution, dried over sodium sulfate and evaporated to dryness. The oil is redissolved in 100 ml of methylene chloride at -78° under nitrogen and 12.82 ml of diisobutylaluminium hydride (1.56M) is added dropwise. The reaction mixture is stirred for 5 min at -78°, quenched with 1 ml of methanol followed by 10 ml of water and filtered through Celite®. The organic phase is separated, dried over sodium sulfate and evaporated to yield the title compound (a).

Workup

  1. washThe reaction mixture is washed with cold 0.5N sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. dissolutionThe oil is redissolved in 100 ml of methylene chloride at -78° under nitrogen
  5. addition12.82 ml of diisobutylaluminium hydride (1.56M) is added dropwise
  6. customquenched with 1 ml of methanol
  7. filtrationfiltered through Celite®
  8. customThe organic phase is separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-6edac8258e7041fc87f5497a814d30dd
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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