m-Chloroperbenzoic acid → 3-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridine 1-oxide

HRID 1592424Notes

Reaction equation

HRID 1592424 reaction equation
[CH2:1]([C:3]([C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[CH2:1]([C:3]([C:8]1[C:9]([CH3:14])=[N+:10]([O-:20])[CH:11]=[CH:12][CH:13]=1)([O:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 672722723-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridine

Product 1

HCID 450971763-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridine 1-oxideYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-ethyl-1-methoxy-propyl)-2-methyl-pyridine (0.176 g, 0.911 mmol) in CH2Cl2 (10 mL) was added 3-chloroperoxybenzoic acid (0.473 g, 2.75 mmol). The mixture was stirred for 16 h and concentrated by evaporation under vacuum. The residue was purified by flash chromatography on a silica gel column (6:1 EtOAc/MeOH), affording 3-(1-ethyl-1-methoxy-propyl)-2-methyl-pyridine I-oxide as a white solid (0.188 g, 98%). 1H NMR (CDCl3) δ 0.74 (t, 6H, J=7.5 Hz), 1.94 (q, 4H, J=7.5 Hz), 2.80 (s, 3H), 3.01 (s, 3H), 7.07-7.10 (m, 1H), 7.21 (d, 1H, J=8.1 Hz), 8.27 (d, 1H, J=6.3 Hz).

Workup

  1. concentrationconcentrated by evaporation under vacuum
  2. customThe residue was purified by flash chromatography on a silica gel column (6:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-ba029d99da6f440e82e453ad64eb16e1
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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