Aluminium lithium hydride → [6-(2,6-Diethylphenyl)-2-methyl-4-methylsulfanyl-pyridin-3-yl]-methanol

HRID 1392667Notes

Reaction equation

HRID 1392667 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[C:16]([S:17][CH3:18])=[CH:15][C:14]([C:19]2[C:24]([CH2:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:27][CH3:28])=[N:13][C:12]=1[CH3:29])C>C1COCC1>[CH2:27]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH2:25][CH3:26])[C:19]=1[C:14]1[N:13]=[C:12]([CH3:29])[C:11]([CH2:10][OH:9])=[C:16]([S:17][CH3:18])[CH:15]=1)[CH3:28]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 669940156-(2,6-Diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester

Product 1

HCID 59678352[6-(2,6-Diethylphenyl)-2-methyl-4-methylsulfanyl-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)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester (125 mg) in THF (5 mL) at 0° C. The mixture is warmed to room temperature and stirred for 1 hour, 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 to give [6-(2,6-diethyl-phenyl)-2-methyl-4-methylsulfanyl-pyridin-3-yl]-methanol.

Workup

  1. temperaturecooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. filtrationThe mixture is filtered through Celite
  5. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-e2cf9c3870d047ea9c99faf4e4faf1c7
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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