Aluminium lithium hydride → HCID 59770289, compound

HRID 2218673Notes

Reaction equation

HRID 2218673 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O.[OH-].[Na+]>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH2:20][NH2:21])[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59770237HCID 59770237, compound

Product 1

HCID 59770289HCID 59770289, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterCatalyst2×HCID 14798Sodium HydroxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 1.0 g (3.25 mmol) of the corresponding nitrile (prepared as described in Example 81) in diethyl ether (70 mL). Add lithium aluminum hydride (250 mg, 6.6 mmol) and stir at room temperature for 3 h. Quench the reaction by adding 8 drops water, 8 drops 5N NaOH and 16 drops water. Filter the inorganic solids and wash with ether. After drying (MgSO4) and concentration, the title compound was obtained in 98% yield as a colorless oil, MS (ES) 312 (N+1). HPLC shows 98% purity.

Workup

  1. customQuench
  2. customthe reaction
  3. filtrationFilter the inorganic solids
  4. washwash with ether
  5. customAfter drying
  6. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-54efa20eacf64117b66724d7e7eff413
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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