Acetic Acid → 4-Acetoxy-2-azetidinone
Reaction equation
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].[C:6]([O-:9])(=[O:8])[CH3:7].[Na+].C(O)(=O)C>C(#N)C.[Ru](Cl)(Cl)Cl>[C:6]([O:9][CH:4]1[NH:1][C:2](=[O:5])[CH2:3]1)(=[O:8])[CH3:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
0.71 g of azetidine-2-one and 0.82 g of anhydrous sodium acetate were suspended in 20 ml of acetonitrile and cooled to -5° C., to which 10 ml of acetonitrile containing 0.26 g of ruthenium trichloride.3H2O was added. 3.8 ml of acetic acid containing 40% peracetic acid was carefully dropped thereto so as to maintain the temperature not higher than 0° C., then continuously stirred at 0° C. for 30 minutes. The solvent was distilled off under reduced pressure at a temperature not higher than 40° C., and subjected to silica gel chromatography (eluent: n-hexane:ethyl acetate=1:1) for purification to obtain 0.92 g of the title compound (yield 71%).
Workup
- addition3H2O was added
- distillationThe solvent was distilled off under reduced pressure at a temperature not higher than 40° C.
- customsubjected to silica gel chromatography (eluent: n-hexane:ethyl acetate=1:1) for purification
Sources & evidence
- ORD record
- ord-86272f1dc89944069954dfa6139e503f
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081239
Reaction notes
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