m-Chloroperbenzoic acid → 2-(3-Oxo-3-tert-butoxy-1-propenyl)pyridine 1-oxide

HRID 499401Notes

Reaction equation

HRID 499401 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].ClC1C=CC=C(C(OO)=[O:24])C=1>C(OCC)(=O)C>[O-:24][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10899753(E)-tert-Butyl 3-(pyridin-2-yl)acrylate

Product 1

HCID 597502862-(3-Oxo-3-tert-butoxy-1-propenyl)pyridine 1-oxideYield 96.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (E)-3-(2-pyridyl)-2-propenoate (2.05 g, 10.0 mmol) was dissolved in ethyl acetate (10 ml), and 3-chloroperbenzoic acid (ca. 70%, 2.35 g, 10.5 mmol) was added thereto. The mixture was stirred at room temperature overnight. The reaction mixture was subjected to a silica gel (100 g) column chromatography. The fractions eluted with ethyl acetate-ethanol (5:1, v/v) were collected and concentrated to give the title compound (2.14 g, 96%).

Workup

  1. washThe fractions eluted with ethyl acetate-ethanol (5:1
  2. customv/v) were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a74cb2fe91074a4e88eb6ce6ea634761
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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