Aluminium lithium hydride → HCID 66707698, compound

HRID 1690865Notes

Reaction equation

HRID 1690865 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9]([NH:11][CH3:12])=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][NH:11][CH3:12])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66707598HCID 66707598, compound

Product 1

HCID 66707698HCID 66707698, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-cyclohex-3-enyl-N-methyl-propionamide (15.5 g, 92.7 mmol) in 55 ml of tetrahydrofuran was added dropwise over a period of 25 min to a suspension of lithium aluminium hydride (95% purity, 5.3 g, 139 mmol, corrected) in 120 ml of tetrahydrofuran at 0° C. under stirring. The mixture was refluxed for 4 hours, stirred overnight at room temperature and quenched with 2 M aqueous NaOH, diluted with tetrahydrofuran, stirred and filtered. The filtrate was concentrated and the residue was acidified with 1 M aqueous HCl and washed with dichloromethane. The aqueous phase was basified with 1 M aqueous NaOH, and extracted with ethyl acetate. The organic extract was dried and concentrated to obtain the title compound (9.38 g, 66% yield) as pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. stirringstirred overnight at room temperature
  3. customquenched with 2 M aqueous NaOH
  4. additiondiluted with tetrahydrofuran
  5. stirringstirred
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. washwashed with dichloromethane
  9. extractionextracted with ethyl acetate
  10. extractionThe organic extract
  11. customwas dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-49ad4b5246e74dbb9cb0e4c8b4b16169
Source dataset
uspto-grants-2012_04
Patent number
US08153689B2

Reaction notes

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