4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine → 2-(3,4,5-Trimethoxyphenyl)pyridine-4-carboaldehyde

HRID 1634894Notes

Reaction equation

HRID 1634894 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([C:5]2[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=[CH:7][N:6]=2)[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

4

Reactant 1

HCID 161259364-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine

Product 1

HCID 186750102-(3,4,5-Trimethoxyphenyl)pyridine-4-carboaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

4-Hydroxymethyl-2-(3,4,5-Trimethoxyphenyl)pyridine (1.01 g) was dissolved in benzene (10 mL), and to the solution activated manganese dioxide (purity: 85%, 3.78 g) was added. The mixture was stirred at room temperature for 5 hours, and activated manganese dioxide (purity: 85%, 3.78 g) was additionally added. The mixture was stirred overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9b766fb091704174bc69a6d4a7d607b2
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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