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

HRID 1392626Notes

Reaction equation

HRID 1392626 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-44873d6c25fa483aa04b0b20676f340d
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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