Aluminium lithium hydride → HCID 59678289, compound

HRID 251617Notes

Reaction equation

HRID 251617 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][C:14]([C:20]2[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:28][CH3:29])=[N:13][C:12]=1[CH3:30])C>C1COCC1.CCOCC>[CH2:28]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([CH2:26][CH3:27])[C:20]=1[C:14]1[N:13]=[C:12]([CH3:30])[C:11]([CH2:10][OH:9])=[C:16]([O:17][CH2:18][CH3:19])[CH:15]=1)[CH3:29]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66993598HCID 66993598, compound

Product 1

HCID 59678289HCID 59678289, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (1 M in THF, 20 mL) is added dropwise to a solution of 6-(2,6-diethyl-phenyl)-4-ethoxy-2-methyl-nicotinic acid ethyl ester (2.3 g, 6.7 mmol) in THF (20 mL). The reaction mixture is stirred at room temperature for 4 hours, diluted with ether (10 mL), and quenched with Na2SO4.10H2O (10 g). The resulting mixture is stirred for one hour, filtered through Celite, and concentrated in vacuo to give [6-(2,6-diethyl-phenyl)-4-ethoxy-2-methyl-pyridin-3-yl]-methanol.

Workup

  1. customquenched with Na2SO4.10H2O (10 g)
  2. stirringThe resulting mixture is stirred for one hour
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f304c1f849c4ab6848fa4d774842779
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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