Imidazole → 1-Allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrroline

HRID 1029625Notes

Reaction equation

HRID 1029625 reaction equation
C(Cl)Cl.[CH2:4]([O:7][C:8]([N:10]1[CH2:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][CH:11]1[CH2:18][OH:19])=[O:9])[CH:5]=[CH2:6].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(OCC)(=O)C.O>[CH2:4]([O:7][C:8]([N:10]1[CH2:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][CH:11]1[CH2:18][O:19][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:9])[CH:5]=[CH2:6]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 199001161-Allyloxycarbonyl-4-acetyl-2-hydroxymethyl-3-pyrroline

Product 1

HCID 216468461-Allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrrolineYield 38.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride solution (50 ml) of 1-allyloxycarbonyl-4-acetyl-2-hydroxymethyl-3-pyrroline (2.5 g) and imidazole (1.51 g) was added tert-butyldimethylsilyl chloride (2.5 g) under ice-cooling. The mixture was then stirred at room temperature for one day, followed by addition of water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate twice. The organic layers were combined, washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 1-allyloxycarbonyl-4-acetyl-2-tert-butyldimethylsilyloxymethyl-3-pyrroline (1.45 g).

Workup

  1. temperaturecooling
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate twice
  4. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationFinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-25b376efcccc4c77b972073ec6b979da
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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