Aluminium lithium hydride → HCID 178519339, compound

HRID 574695Notes

Reaction equation

HRID 574695 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](O)=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178524171HCID 178524171, compound

Product 1

HCID 178519339HCID 178519339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1H-benzo[d]imidazole-5-carboxylic acid (10 mmol, 1 eq.) was dissolved in 30 mL THF and cooled down to −78° C. 20 mL 1 M solution of lithium aluminium hydride (20 mmol, 2 eq.) were added slowly. After stirring at ambient temperature for 10 hours the reaction was quenched with methanol. The solvent was removed, 50 mL aqueous solution of sodium hydrogen carbonate was added and extracted with 50 mL ethyl acetat three times. The combined organic layers were dried over sodium sulfate, filtrated and the solvent was removed under reduced pressure. The product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.

Workup

  1. customwas quenched with methanol
  2. customThe solvent was removed
  3. addition50 mL aqueous solution of sodium hydrogen carbonate was added
  4. extractionextracted with 50 mL ethyl acetat three times
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltrated
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by means of flash-chromatography

Sources & evidence

ORD record
ord-8f7047d57aa347bf96ed3a311bbc1cca
Source dataset
uspto-grants-2015_05
Patent number
US09034907B2

Reaction notes

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