Aluminium lithium hydride → HCID 59780459, compound

HRID 222557Notes

Reaction equation

HRID 222557 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH2:18][C:19](OCC)=[O:20])=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH2:18][CH2:19][OH:20])=[CH:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59780469HCID 59780469, compound

Product 1

HCID 59780459HCID 59780459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.50 g (1.64 mmol) of 16, dissolved in 5 ml of THF, was slowly added dropwise to a suspension of 0.12 g (3.27 mmol) of lithium aluminium hydride (LiAlH4, powder) in 10 ml of THF with stirring and ice-cooling. The mixture was stirred for 3 h at RT, excess LiAlH4 was destroyed by addition of saturated ammonium chloride solution, and the mixture was extracted 2× with ethyl acetate. The combined organic phases were dried, the solvent was removed, and the residue was purified by column chromatography (ethyl acetate/cyclohexane), giving a colourless solid (compound 17).

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred for 3 h at RT
  3. customexcess LiAlH4 was destroyed by addition of saturated ammonium chloride solution
  4. extractionthe mixture was extracted 2× with ethyl acetate
  5. customThe combined organic phases were dried
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography (ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-b0151d2e52ba4891be2aa7dc925d0d34
Source dataset
uspto-grants-2012_06
Patent number
US08207345B2

Reaction notes

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