Pyridine N-Oxide → 4-[2-(2-Ethoxycarbonyl-ethyl)-3-(6-oxo-hexyl)-phenoxy]-butyric acid ethyl ester

HRID 1670151Notes

Reaction equation

HRID 1670151 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[N+]1([O-:36])C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[O:36])[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

5

Reactant 3

HCID 12753Pyridine N-OxideHCID 516892Sodium BicarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 575865124-[2-(2-Ethoxycarbonyl-ethyl)-3-(6-oxo-hexyl)-phenoxy]-butyric acid ethyl esterYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[3-(6-Bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (10.0 g, 21.2 mmol), pyridine N-oxide (10.06 g, 106 mmol), and sodium bicarbonate (10.0 g, 119 mmol) were heated at reflux with vigorous stirring in toluene (100 mL) for 24 h. The mixture was cooled to room temperature and filtered. The filtrate was then concentrated under reduced pressure and the crude material was purified by column chromatography using 30% ethyl acetate-hexanes as eluant to give the title compound (7.0 g, 81%) as an oil.

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationThe filtrate was then concentrated under reduced pressure
  4. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-b57696d913fc42febfe997aab12e498e
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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