4-(2-Pyridyl)Benzoic Acid → (4-(Pyridin-2-yl)phenyl)methanol

HRID 1459632Notes

Reaction equation

HRID 1459632 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8216924-(2-Pyridyl)Benzoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1515239(4-(Pyridin-2-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(pyrid-2-yl)benzoic acid(1.01 g, 5.09 mmol) in tetrahydrofuran (15 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (5.09 mL, 5.09 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 3 hours, cooled to 0° C., and quenched by dropwise addition of water (0.25 mL), 4N aq. NaOH (0.25 mL), and water (0.75 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, 4-8% MeOH in CH2Cl2) to afford the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.25 mL), 4N aq. NaOH (0.25 mL), and water (0.75 mL)
  3. filtrationThe reaction was filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was chromatographed (silica gel, 4-8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dd6879b2577f4901a42fa7f5a4188b9e
Source dataset
uspto-grants-1998_12
Patent number
US05854264

Reaction notes

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