Hydrochloric Acid → Ethyl 4-[2-(2,5-dimethylpyrrole-1-yl)ethoxy]acetoacetate

HRID 2298441Notes

Reaction equation

HRID 2298441 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]([CH2:10][CH2:11][OH:12])[C:6]([CH3:9])=[CH:7][CH:8]=1.Cl[CH2:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>O1CCCC1.O>[CH3:3][C:4]1[N:5]([CH2:10][CH2:11][O:12][CH2:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]([CH3:9])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 959631-(2-Hydroxyethyl)-2,5-dimethylpyrrole

Product 1

HCID 11369154Ethyl 4-[2-(2,5-dimethylpyrrole-1-yl)ethoxy]acetoacetateYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

32 g of sodiumhydride (60% oil dispersion) was added to 500 ml of tetrahydrofuran, and 56 g (0.4 mol) of 2-(2,5-dimethylpyrrole-1-yl)ethanol obtained in Preparation Example 1 was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to 0° C., and a solution obtained by dissolving 65.84 g (0.4 mol) of ethyl 4-chloroacetoacetate in 200 ml of tetrahydrofuran was added thereto dropwise over 2 hours. The mixture was stirred at room temperature for 16 hours and then adjusted to pH 6 to 7 with 3N hydrochloric acid. A sufficient amount of water was added to dissolve solid precipitates formed, and the reaction mixture was extracted two times with 600 ml and 100 ml of ethyl acetate, respectively. Combined ethyl acetate extract was dried over anhydrous magnesium sulfate, treated with decolorizing carbon, and then, the solvent was distilled off under a reduced pressure, to obtain 96.2 g of the titled compound as a pale yellow oil (yield: 90%).

Workup

  1. customobtained in Preparation Example 1
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customa solution obtained
  5. additionwas added
  6. waitdropwise over 2 hours
  7. stirringThe mixture was stirred at room temperature for 16 hours
  8. dissolutionto dissolve solid
  9. customprecipitates
  10. customformed
  11. extractionthe reaction mixture was extracted two times with 600 ml and 100 ml of ethyl acetate
  12. extractionCombined ethyl acetate extract
  13. dry with materialwas dried over anhydrous magnesium sulfate
  14. additiontreated with decolorizing carbon
  15. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-a64c17012b894b379b078732d70d8f60
Source dataset
uspto-grants-2002_12
Patent number
US06492523B2

Reaction notes

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