Water → (5-Phenylpyridin-3-yl)methanol

HRID 1901118Notes

Reaction equation

HRID 1901118 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[C:11]([CH:16]=2)[C:12](OC)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:13][CH2:12][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20100220Methyl 5-phenylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22254272(5-Phenylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-phenylnicotinate (640 mg) in THF (20 mL) at 0° C. was added LiAlH4 (3 mL of a 1M solution). After 1 h, H2O (0.12 mL), 15% sodium hydroxide (0.12 mL) and H2O (0.36 mL) were added successively. The mixture was filtered, washing with EtOAc. The filtrate was concentrated and chromatographed (silica gel; EtOAc/hexane (4:1-5:1)) to provide the title compound as a solid.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customchromatographed (silica gel; EtOAc/hexane (4:1-5:1))

Sources & evidence

ORD record
ord-63139cbf2cee41b3889be66f538a825e
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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