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

HRID 1242403Notes

Reaction equation

HRID 1242403 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]-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2.6 g (8.40 mmol) of the above prepared [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester dissolved in 15 ml of dry tetrahydrofuran was added under an argon atmosphere within 15 minutes to a stirred suspension of 0.38 g (10 mmol) of lithium aluminum 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 into the reaction mixture, followed by water, drop after drop, under argon, with stirring and cooling until the gas evolution ceased. The reaction mixture was then diluted with 50 ml of ethyl acetate, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated i. V. and the residue was chromatographed on SiO2 with a mixture of dichloromethane and tert.-butyl methyl ether (4/1 vol./vol.) as eluent. Thereby, 1.88 g of the title compound was obtained as white solid.

Workup

  1. stirringunder argon, with stirring
  2. temperaturecooling until the gas evolution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated i
  6. customand the residue was chromatographed on SiO2 with a mixture of dichloromethane and tert.-butyl methyl ether (4/1 vol./vol.) as eluent

Sources & evidence

ORD record
ord-f6e2176e7184458f8fa0ccdebbbd4732
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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