Aluminium lithium hydride → HCID 178519949, compound

HRID 1008236Notes

Reaction equation

HRID 1008236 reaction equation
C([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][C:6]1[NH:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178470180HCID 178470180, compound

Product 1

HCID 178519949HCID 178519949, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.75 g ethyl-4-phenylimidazole-2-carboxylate in 20 mL tetrahydrofuran was added a suspension of 0.5 g lithium aluminum hydride in 30 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature overnight, poured into 100 mL of ice water and extracted with 2×100 mL of ethyl acetate. The combined extracts were washed with 2×100 mL of brine, dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to yield 2 g of 2-hydroxymethyl-4-phenylimidazole which was used in the next step without further purification or characterization.

Workup

  1. extractionextracted with 2×100 mL of ethyl acetate
  2. washThe combined extracts were washed with 2×100 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-22e125193d8b4f59b74d4c1f8307fca4
Source dataset
uspto-grants-2004_09
Patent number
US06797824B2

Reaction notes

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