HCID 22318750, compound → HCID 22318798, compound

HRID 481107Notes

Reaction equation

HRID 481107 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][N:5]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 1

HCID 22318750HCID 22318750, compound

Product 1

HCID 22318798HCID 22318798, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 321 mg (1.75 mmol) of (2-dimethoxymethyl-pyridin-3-yl)-methanol and 763 mg (8.77 mmol) of MnO2 in 10 mL of toluene is refluxed for 1.5 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated to yield 271 mg of 2-dimethoxymethyl-pyridine-3-carbaldehyde. 1H NMR (CDCl3) δ10.30 (s, 1H), 8.30 (d, 1H), 8.10 (d, 1H), 7.30 (m, 1H), 5.40 (s, 2H), 4.40 (s, 6H).

Workup

  1. temperatureis refluxed for 1.5 hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-b8acf1a4383d4352ae3b0c9feca6c60a
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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