m-Chloroperbenzoic acid → HCID 22939454, compound

HRID 748149Notes

Reaction equation

HRID 748149 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][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[CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 591086993-Pyridin-2-yl-propionic acid tert-butyl ester

Product 1

HCID 22939454HCID 22939454, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(2-pyridyl)propanoate (1.0 g, 5.0 mmol) was dissolved in ethyl acetate (5 ml), and 3-chloroperbenzoic acid (ca. 70%, 1.3 g, 5.2 mmol) was added thereto. The reaction mixture was subjected to a silica gel (50 g) column chromatography and eluted with ethyl acetate-ethanol (5:1, v/v) to give the titled compound (0.9 g, 80%). 1H-NMR (CDCl3) δ: 1.41 (9H, s), 2.76 (2H, t, J=7.1 Hz), 3.17 (2H, t, J=7.1 Hz), 7.15-7.32 (3H, m), 8.24 (1H, d, J=5.7 Hz).

Workup

  1. washeluted with ethyl acetate-ethanol (5:1

Sources & evidence

ORD record
ord-2e703d35104944dbb770afd637b8c0ac
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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