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

HRID 420403Notes

Reaction equation

HRID 420403 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, 1 19 mmol) were heated at reflux with vigorous stirring in toluene (100 mL) for 24 hr. The mixture was cooled down and filtered. The filtrate was then evaporated under vacuo and the crude material was purified by column chromatography using 30% EtOAc-Hexane as eluant to give the title compound (7.0 g, 81%) as an oil. HR-MS-EI(+): calculated for C23H34O6 [M] 406.2350, found 406.2355.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was cooled down
  3. filtrationfiltered
  4. customThe filtrate was then evaporated under vacuo
  5. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-5d0e8027f4c14316b9aff85627855b0a
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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