Aluminium lithium hydride → HCID 178519997, compound

HRID 2072799Notes

Reaction equation

HRID 2072799 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[N:9][C:8]=2[C:12](OCC)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:13][CH2:12][C:8]1[N:9]=[CH:10][NH:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178470301HCID 178470301, compound

Product 1

HCID 178519997HCID 178519997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4.5 g of ethyl 5-phenylimidazole-4-carboxylate [J. Het. Chem. 20, 1417 (1983)]in 50 ml of dry tetrahydrofuran at 5° C. was added in portions 1.1 g of lithium aluminum hydride. The resulting reaction mixture was stirred at room temperature for several hours and was then cooled to 10° C. and quenched with 1N hydrochloric acid until the evolution of hydrogen stopped. The reaction mixture was further diluted with water and extracted several times with ethyl acetate. The extracts were combined, dried and concentrated to give a white solid which has triturated with hexane and filtered, 3.2 g.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then cooled to 10° C.
  3. customquenched with 1N hydrochloric acid until the evolution of hydrogen
  4. additionThe reaction mixture was further diluted with water
  5. extractionextracted several times with ethyl acetate
  6. customdried
  7. concentrationconcentrated
  8. customto give a white solid which
  9. customhas triturated with hexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-52b7e8e4d9ab4b76be978a8ea7de1df6
Source dataset
uspto-grants-1990_04
Patent number
US04914207

Reaction notes

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