Aluminium lithium hydride → HCID 57656050, compound

HRID 2041148Notes

Reaction equation

HRID 2041148 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH3:21])([CH3:20])[CH2:9][CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>C(OCC)C>[CH3:7][C:8]([CH3:21])([CH3:20])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][NH2:17])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57656629HCID 57656629, compound

Product 1

HCID 57656050HCID 57656050, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Mix lithium aluminum hydride (1.0 g, 26.6 mmol) and anhydrous ethyl ether (70 mL) under nitrogen atmosphere. Stir and cool to 0° C. in an ice bath. Add dropwise a solution of 4-(3,3-dimethylbutoxy)-benzonitrile (1.8 g, 8.87 mmol) in anhydrous ethyl ether (20 mL). Stir for 2 h at 0° C., remove the ice bath and stir at ambient temperature for 18 h. Cool the reaction flask in an ice bath and add carefully dropwise and sequentially water (1 mL), 2N aqueous NaOH (1 mL), and water (2 mL). Stir for 30 min, filter, separate the organic layer, dry over Na2SO4 and concentrate in vacuo to obtain the title compound (1.62 g, 88%). MS (ES+) m/z: 191 (M+H—NH3)+.

Workup

  1. stirringStir for 2 h at 0° C.
  2. customremove the ice bath
  3. stirringstir at ambient temperature for 18 h
  4. temperatureCool the reaction flask in an ice bath
  5. additionadd carefully dropwise
  6. stirringStir for 30 min
  7. filtrationfilter
  8. customseparate the organic layer
  9. dry with materialdry over Na2SO4
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-58eaff2d7c914eeb8d8f364371268f38
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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