Aluminium lithium hydride → (6-(3-(Trifluoromethoxy)phenyl)pyridin-3-yl)methanol

HRID 363191Notes

Reaction equation

HRID 363191 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:20][C:2]([F:1])([F:19])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 247299956-[3-(Trifluoromethoxy)phenyl]nicotinic acid

Product 1

HCID 24729919(6-(3-(Trifluoromethoxy)phenyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-trifluoromethoxyphenyl)-5-carboxy pyridine (2.0 g, 7.06 mmol) in tetrahydrofuran (15 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (7.07 mL, 7.07 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 4 hours, cooled to 0° C., and quenched by dropwise addition of saturated Na2SO4 (1.0 mL). The reaction was diluted with diethylether, filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, 50% EtOAc in hexanes) to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of saturated Na2SO4 (1.0 mL)
  3. additionThe reaction was diluted with diethylether
  4. filtrationfiltered through a pad of Celite
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was chromatographed (silica gel, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-97a479a502b14cf6911026f0b8b53d83
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

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