Ethyl Acetate → HCID 15117220, compound

HRID 1029616Notes

Reaction equation

HRID 1029616 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]=[C:9]([C:12]#[C:13][Si](C)(C)C)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C(=O)([O-])[OH:19].[Na+].C(OCC)(=O)C>S(=O)(=O)(O)O.O1CCCC1.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]=[C:9]([C:12](=[O:19])[CH3:13])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 15117219HCID 15117219, compound

Product 1

HCID 15117220HCID 15117220, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-allyloxycarbonyl-3-trimethylsilylethynyl-3-pyrroline (7.60 g), mercuric sulfate (0.9 g) and sulfuric acid (5 drops) in a mixture of tetrahydrofuran (76 ml) and water (23 ml) was stirred at room temperature overnight. After confirming the disappearance of the starting material, to the mixture were added saturated aqueous sodium hydrogen carbonate and ethyl acetate. The aqueous layer was extracted with ethyl acetate twice, and the combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine successively, dried over magnesium sulfate. Evaporation of the solvent gave 1-allyloxycarbonyl-3-acetyl-3-pyrroline (2.3 g).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate twice
  2. washthe combined organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-33a870f654044c1698043cd52eca07f8
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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