Water → HCID 10890704, compound

HRID 278405Notes

Reaction equation

HRID 278405 reaction equation
C([CH:4]([CH2:10][CH2:11][C:12](=[O:23])[CH:13]([C:17]1[O:21][N:20]=[C:19]([CH3:22])[CH:18]=1)[C:14](=O)[CH3:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)C.C(N(CC)CC)C.O>CO>[CH2:8]([O:7][C:5]([CH:4]1[CH2:10][CH2:11][C:12](=[O:23])[C:13]([C:17]2[O:21][N:20]=[C:19]([CH3:22])[CH:18]=2)=[C:14]1[CH3:15])=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22628440HCID 22628440, compound

Product 1

HCID 10890704HCID 10890704, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.85 g of the obtained ethyl 2-acetyl-5,7-dioxo-6-(3-methylisooxazol-5-yl)octanoate was dissolved in 5 ml of methanol and 0.32 g of triethylamine was added. The resulting solution was stirred at room temperature for 2 hours and then heated at reflux for 3 hours. After cooling, water was added to the reaction solution to extract with ethyl acetate. The organic layer was washed with saturated salt water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The obtained residue was purified on silica gel column chromatography to give 0.27 g of the title compound as a colorless liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionto extract with ethyl acetate
  5. washThe organic layer was washed with saturated salt water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation
  8. customThe obtained residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-0674f54ea82a453a9e899f6c4c382e95
Source dataset
uspto-grants-2002_03
Patent number
US06359143B1

Reaction notes

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