Aluminium lithium hydride → {6-[2-(Trifluoromethyl)phenyl]pyridin-3-yl}methanol

HRID 363195Notes

Reaction equation

HRID 363195 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][N:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 247299916-[2-(Trifluoromethyl)phenyl]pyridine-3-carboxylic acid

Product 1

HCID 24729917{6-[2-(Trifluoromethyl)phenyl]pyridin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-Trifluoromethylphenyl)-5-carboxypyridine (220 mg, 1.23 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (1.23 mL, 1.23 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 16 hours, cooled to 0° C., and quenched by dropwise addition of water (0.05 mL), 2.5N aq. NaOH (0.05 mL), and water (0.15 mL). Sodium sulfate was added, the reaction filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, CH2Cl2 then EtOAc) to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.05 mL), 2.5N aq. NaOH (0.05 mL), and water (0.15 mL)
  3. additionSodium sulfate was added
  4. filtrationthe reaction filtered through a pad of Celite
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was chromatographed (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-332f1a71008e47208d4868b94fa3fe39
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

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