Water → 2-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

HRID 890449Notes

Reaction equation

HRID 890449 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([CH3:21])=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C(OCC)(=O)C>[CH3:21][C:6]1[C:5]([CH2:4][CH2:3][OH:2])=[CH:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:13][CH:12]=2)[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67072318[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

Product 1

HCID 219358312-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanolYield 79.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2.6 g (8.40 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester in 15 ml of dry tetrahydrofuran were added under an argon atmosphere within 15 minutes to a stirred suspension of 0.38 g (10 mmol) of lithium aluminium hydride in 5 ml of tetrahydrofuran. The reaction was exothermic. Subsequently, the mixture was stirred at room temperature for 1 hour. Then, 1 ml of ethyl acetate was dropped to the reaction mixture, followed by water, drop after drop, under argon, with stirring and cooling until the gas evolution ceased. The reaction mixture was diluted with 50 ml of ethyl acetate, dried with anhydrous sodium sulfate and filtered. The filtrate was evaporated and the residue was chromatographed on silicagel with a mixture of dichloromethane and tert.-butyl methyl ether (4:1 vol./vol.) as eluent. 1.88 g (79.5% of theory) of 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol was obtained as white solid.

Workup

  1. stirringunder argon, with stirring
  2. temperaturecooling until the gas evolution
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed on silicagel with a mixture of dichloromethane and tert.-butyl methyl ether (4:1 vol./vol.) as eluent

Sources & evidence

ORD record
ord-7afc8e3c77454d7c960141796fec60c5
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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