Isopropanol → HCID 15117309, compound

HRID 1029669Notes

Reaction equation

HRID 1029669 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]([CH:12]([OH:14])[CH3:13])[CH2:9][N:8]1[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=[O:6])[CH:2]=[CH2:3].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[C:12]([CH:10]1[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[N:8]([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:9]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 15117308HCID 15117308, compoundHCID 131709961Jones' reagent

Product 1

HCID 15117309HCID 15117309, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1,2-bis(allyloxycarbonyl)-4-(1-hydroxyethyl)pyrazolidine (13 g) in acetone (260 ml) was added dropwise Jones Reagent (2.67N, 34 ml) at 0° C. After stirring for 1 hour, to the reaction mixture was added dropwise 2-propanol (200 ml) and the reaction mixture was stirred at 0° C. for 1 hour. The precipitate was filtered off and the filtrate was evaporated to give a residual oil, which was extracted with ethyl acetate and the organic layer was separated, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give 4-acetyl-1,2-bis(allyloxycarbonyl)pyrazolidine (9.18 g).

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 1 hour
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated
  4. customto give a residual oil, which
  5. extractionwas extracted with ethyl acetate
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent
  10. customgave an oil, which
  11. customwas chromatographed on silica gel (300 ml)
  12. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-78ad766ccb1c4df3a4e55722e2a457e4
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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