Methanol → 2-Methyl-6-phenylpyridin-3-ol

HRID 563953Notes

Reaction equation

HRID 563953 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([CH:13]=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C[OH:18]>>[CH3:13][C:11]1[C:10]([OH:18])=[CH:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 135224166-Phenylpyridine-2-carbaldehyde

Product 1

HCID 121555782-Methyl-6-phenylpyridin-3-olYield 99%

Procedure

To a solution of 0.250 g (1.36 mmol) of 6-phenyl-2-pyridine aldehyde in 5 mL of methanol was added sodium borohydride (0.08 g, 2.05 mmol) portionwise with stirring under N2 at ambient temperature. After 10 min, the reaction was quenched with 5 mL of saturated aqueous ammonium chloride solution. This solution was extracted with 3×50 mL EtOAc. The organic fractions were pooled, dried over Na2SO4 and concentrated. After removing the volatiles in vacuo, the resultant yellow oil was chromatographed on silica with 10% EtOAc/hexanes. Clean fractions were combined and the volatiles were removed to provide 0.250 g of 2-methylhydroxyl-6-phenyl pyridine as a clear oil (>99%).

Workup

  1. customthe reaction was quenched with 5 mL of saturated aqueous ammonium chloride solution
  2. extractionThis solution was extracted with 3×50 mL EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customAfter removing the volatiles in vacuo
  6. customthe resultant yellow oil was chromatographed on silica with 10% EtOAc/hexanes
  7. customthe volatiles were removed

Sources & evidence

ORD record
ord-486d11f6ff4e46fb935c5dc9ea17f955
Source dataset
uspto-grants-2011_11
Patent number
US08067609B2

Reaction notes

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