Hydrochloric Acid → HCID 86641944, compound

HRID 384124Notes

Reaction equation

HRID 384124 reaction equation
[O:1]=[C:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:12][CH:11]=1)[CH2:3][C:4](OCC)=[O:5].[Cl-].[OH:32][NH3+:33].[OH-].[Na+].Cl>O1CCOCC1>[OH:32][NH:33][C:4](=[O:5])[CH2:3][C:2](=[O:1])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21645Hydroxylamine HClHCID 68430400HCID 68430400, compound

Product 1

HCID 86641944HCID 86641944, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-oxo-4-(4-((2-phenoxybenzyl)oxy)phenyl)butanoate (40 mg) in 1,4-dioxan (0.12 ml), 9 mg of hydroxylammonium chloride and 0.1 ml of 2.5N sodium hydroxide were added under ice-cooling, and the reaction solution was stirred at 0° C. for 1.5 hours. Concentrated hydrochloric acid (0.07 ml) was further added, and the reaction solution was stirred at room temperature for 20 minutes. The reaction solution was extracted with chloroform, the combined organic layers were washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., hexane/ethyl acetate (1:1) to afford the title compound as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe reaction solution was stirred at room temperature for 20 minutes
  3. extractionThe reaction solution was extracted with chloroform
  4. washthe combined organic layers were washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744

Sources & evidence

ORD record
ord-7919e7a9044349a1b93bd5e75c6d3379
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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