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

HRID 2290564Notes

Reaction equation

HRID 2290564 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 minutes and 1.45 ml of trimethylsilyl chloride at 0° for 3 hours. 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 diisobutyl-aluminum hydride (1.56M) is added dropwise. The reaction mixture is stirred for 5 minutes 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 diisobutyl-aluminum 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-600b5bf94ee3415aa366421900f76bd3
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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