Aluminium lithium hydride → [6-(2,6-Diethyl-phenyl)-4-methoxy-pyridin-3-yl]-methanol

HRID 251594Notes

Reaction equation

HRID 251594 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]2[C:23]([CH2:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:26][CH3:27])=[N:12][CH:11]=1>C1COCC1.CCOCC>[CH2:26]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH2:24][CH3:25])[C:18]=1[C:13]1[N:12]=[CH:11][C:10]([CH2:9][OH:8])=[C:15]([O:16][CH3:17])[CH:14]=1)[CH3:27]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 596780886-(2,6-Diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester

Product 1

HCID 59678105[6-(2,6-Diethyl-phenyl)-4-methoxy-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (1 M in THF, 15 mL) is added dropwise to a solution of 6-(2,6-diethyl-phenyl)-4-methoxy-nicotinic acid methyl ester (1.5 g, 5 mmol) in THF (10 mL). The reaction mixture is stirred at room temperature for 6 hours, then 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 to give [6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-methanol. 1H NMR (CDCl3) 8.47 (s, 1H), 7.28 (t, 1H), 7.13 (d, 2H), 6.79 (s, 1H), 4.72 (s, 2H), 3.89 (s, 3H), 2.55 (br, 1H), 2.34 (m, 4H), 1.06 (t, 6H).

Workup

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

Sources & evidence

ORD record
ord-d6bb0e2e7ace497eafb9e41020ddc0ad
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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