HCID 67336197, compound → 1-(6-Methoxy-4-methylpyridin-3-yl)propan-1-one

HRID 1671321Notes

Reaction equation

HRID 1671321 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:12])[CH2:10][CH3:11])=[C:5]([CH3:13])[CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 1

HCID 67336197HCID 67336197, compound

Product 1

HCID 673357591-(6-Methoxy-4-methylpyridin-3-yl)propan-1-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1-(6-methoxy-4-methyl-pyridin-3-yl)-propan-1-ol (445 mg, 2.45 mmol, 1 eq.) in CHCl3 (10 ml) is added activated manganese dioxide (4.3 g, 49 mmol, 20 eq.) in one portion at RT. The reaction mixture is heated at reflux for 48 h. After cooling to RT, the mixture is filtered through Celite® (filter material) and concentrated under reduced pressure. The resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane to yield 1-(6-methoxy-4-methyl-pyridin-3-yl)-propan-1-one as a white solid. MS: m/z 180.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 1.2 (t, 3H), 2.55 (s, 3H), 2.95 (q, 2H), 4.00 (s, 3H), 6.60 (s, 1H), 8.65 (s, 1H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 48 h
  3. filtrationthe mixture is filtered through Celite® (filter material)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-2f14d0411c8e4348b7f1aa3853490e95
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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