Aluminium lithium hydride → HCID 16771797, compound

HRID 2080150Notes

Reaction equation

HRID 2080150 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23130570HCID 23130570, compound

Product 1

HCID 16771797HCID 16771797, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4(pyridine-2-ylmethoxy)-benzonitrile described in Preparation Example 170 (1.2 g, 5.70 mmol) in tetrahydrofuran (30 mL) was added lithium aluminum hydride (0.22 g, 5.80 mmol), and the solution was stirred for 2 hours 30 minutes at room temperature. Ice water was added to the reaction solution, which was then stirred for 30 minutes. This mixture was filtered through Celite pad, and washed with ethyl acetate. The filtrate was partitioned, this organic layer was dried over anhydrous magnesium sulfate, then, concentrated, and the title compound (1.1 g, 5.13 mmol, 90%) was obtained.

Workup

  1. stirringwas then stirred for 30 minutes
  2. filtrationThis mixture was filtered through Celite pad
  3. washwashed with ethyl acetate
  4. customThe filtrate was partitioned
  5. dry with materialthis organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d71eb6e304842e0a3e49fa323de5d48
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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