Aluminium lithium hydride → HCID 22241308, compound

HRID 892138Notes

Reaction equation

HRID 892138 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH2:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22241260HCID 22241260, compound

Product 1

HCID 22241308HCID 22241308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 3-[(2-methoxyethoxy)-methoxy]-benzonitrile (3.9 g, 18.8 mmol, example 8) in THF (40 mL) is added LAH (40 mL, 1M in THF). The resulting solution is stirred for 10 min. then the cold bath removed and stirring continued for 2 h. The resulting mixture is cooled to 0° C. then water (1.5 mL) added dropwise followed by NaOH solution (1.5 mL, SM) and water (1.5 mL). The resulting suspension is diluted with ether then filtered through celite. The filtrate is concentrated to give the title compound which is used without further purification. MS (ESI) 211 (M+H)+.

Workup

  1. customthe cold bath removed
  2. stirringstirring
  3. waitcontinued for 2 h
  4. additionwater (1.5 mL) added dropwise
  5. additionThe resulting suspension is diluted with ether
  6. filtrationthen filtered through celite
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-0ad05b757c3d46f4a06e6dbde403bb11
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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