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

HRID 251588Notes

Reaction equation

HRID 251588 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][C:11]=1[CH3:28]>C1COCC1>[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]=[C:11]([CH3:28])[C:10]([CH2:9][OH:8])=[C:15]([O:16][CH3:17])[CH:14]=1)[CH3:27]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 596783046-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester

Product 1

HCID 59678301[6-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (1 M in THF, 1 mL, 1 mmol) is added to a solution of 6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester (122 mg, 0.39 mmol) in THF (5 mL) at 0° C. The mixture is warmed to room temperature and stirred for 2 hours. The mixture is cooled to 0° C. and Na2SO4.10H2O is added to quench the reaction. The mixture is filtered through Celite and the filtrate is concentrated in vacuo. The crude product is purified by PTLC (hexanes/ethyl acetate 3:1) to give [6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-pyridin-3-yl]-methanol as a white solid. 1H NMR: (CDCl3) 7.26 (m, 1H), 7.13 (d, 2H), 6.68 (S, 1H), 4.82 (d, 2H), 3.87 (s, 3H), 2.65 (s, 3H), 2.33 (m, 4H), 1.05 (t, 6H).

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. filtrationThe mixture is filtered through Celite
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe crude product is purified by PTLC (hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-4a7b098bc14a45b58e9e4e41f9905960
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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