Acetic Acid → 4-Oxazolin-2-one, 4-phenyl-
Reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[O-:11][C:12]#[N:13].[K+].C(O)(=O)C.O>C(O)(C)C>[C:5]1([C:3]2[NH:13][C:12](=[O:11])[O:1][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-hydroxyacetophenone (10.0 g, 73.4 mmol) and potassium cyanate (11.9 g, 147 mmol) in isopropanol (50 ml) was added dropwise acetic acid (10.1 ml, 176 mmol) at 50° C., and the mixture was stirred at 50° C. for 5 hours. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give 4.83 g (40.9%) of the desired product as a solid.
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)
Sources & evidence
- ORD record
- ord-1b028d483e4743ef8cf5d6905c8b8dca
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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