Hydrochloric Acid → HCID 11727819, compound

HRID 1826080Notes

Reaction equation

HRID 1826080 reaction equation
[H-].[Na+].[C:3](=O)([O:7]CC)[O:4][CH2:5][CH3:6].[C:11]([C:14]1[CH:15]=[C:16]([CH2:22][CH:23]([CH2:29][CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])(=[O:13])[CH3:12].Cl>C(OCC)(=O)C.C(O)C.C(OCC)C>[CH2:5]([O:4][C:3]([CH2:12][C:11]([C:14]1[CH:15]=[C:16]([CH2:22][CH:23]([CH2:29][CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])=[O:13])=[O:7])[CH3:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 11140416HCID 11140416, compound

Product 1

HCID 11727819HCID 11727819, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To anhydrous diethyl ether (20 mL), sodium hydride (60% oil dispersion, 1.27 g, 52.9 mmol) was added under stirring and cooling with ice. Successively, after diethyl carbonate (2.25 g, 19.0 mmol) was added, the mixture was stirred for 30 minutes at room temperature. Following this, a mixture of ethyl 3-(3-acetyl-4-methoxyphenyl)-2-ethylpropanoate (3.53 g, 12.7 mmol), anhydrous diethyl ether (10 mL) and absolute ethanol (0.24 mL) was added dropwise over 20 minutes, and then the mixture was refluxed for 6 hours. After cooling, the reaction mixture was added slowly to a mixed solution of 2 mol/L hydrochloric acid (45 mL) with ethyl acetate (80 mL) under stirring and cooling with ice. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v) to afford 2.59 g (58%) of the title compound as a pale yellow oil.

Workup

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred for 30 minutes at room temperature
  3. additionwas added dropwise over 20 minutes
  4. temperaturethe mixture was refluxed for 6 hours
  5. temperatureAfter cooling
  6. stirringunder stirring
  7. temperaturecooling with ice
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with ethyl acetate
  10. washwashed with water and brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v)

Sources & evidence

ORD record
ord-9dcb2fd2291541faabe9aa14094cfcba
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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