6-Phenylnicotinic acid → (6-Phenylpyridin-3-yl)methanol

HRID 363185

Reaction equation

HRID 363185 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](O)=[O:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1201186-Phenylnicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22254216(6-Phenylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-phenyl-5-carboxypyridine (520 mg, 2.61 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (2.61 mL, 2.61 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 (0.20 mL), 4N aq. NaOH (0.20 mL), and water (0.60 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, 0-5% MeOH in CH2Cl2) to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.20 mL), 4N aq. NaOH (0.20 mL), and water (0.60 mL)
  3. filtrationThe reaction was filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was chromatographed (silica gel, 0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a3b5c2400dee48e2a5a82e527bf47452
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Linked notes

Loading…