Hydrochloric Acid → HCID 22722110, compound

HRID 1581654Notes

Reaction equation

HRID 1581654 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([C:22](=[O:24])[CH3:23])[CH:21]=1.Cl>C(OCC)(=O)C.C(O)C.O1CCCC1.CCOCC>[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([C:22](=[O:24])[CH2:23][C:3]([O:7][CH2:8][CH3:9])=[O:10])[CH:21]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 22722111HCID 22722111, compound

Product 1

HCID 22722110HCID 22722110, compoundYield 52.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To dehydrated ether (15 mL) was added sodium hydride (940 mg, 23.5 mmol) under cooling with ice and stirring, and following this, diethyl carbonate (1.66 g, 14.1 mmol) was added, which was stirred for 30 minutes at room temperature. Next, 5′-(1,3-dioxolane-2-yl)-2′-methoxyacetophenone (2.08 g, 9.36 mmol), dehydrated tetrahydrofuran (20 mL) and ethanol (0.05 mL) were mixed and added dropwise slowly. After completion of the dropwise addition, the mixture was refluxed for 7 hours. After allowed to stand for cooling, the reaction mixture was poured slowly into a solution of 2 mol/L hydrochloric acid (20 mL) and ethyl acetate (30 mL) under cooling with ice and stirring. After separated the organic layer, the aqueous layer was extracted with ethyl acetate. Respective organic layers were combined, washed with water and saturated brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v) to obtain 1.44 g (52%) of the title compound as a pale yellow oil.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. stirringwhich was stirred for 30 minutes at room temperature
  4. additionadded dropwise slowly
  5. additionAfter completion of the dropwise addition
  6. temperaturethe mixture was refluxed for 7 hours
  7. temperaturefor cooling
  8. temperatureunder cooling with ice
  9. stirringstirring
  10. customAfter separated the organic layer
  11. extractionthe aqueous layer was extracted with ethyl acetate
  12. washwashed with water and saturated brine in sequence
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated
  15. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v)

Sources & evidence

ORD record
ord-6babf6a490c747678247bd945f68fb93
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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