N-methoxy-N-methylisoxazole-3-carboxamide → 1-(3-Isoxazolyl)-2-propen-1-one
Reaction equation
CON(C)[C:4]([C:6]1[CH:10]=[CH:9][O:8][N:7]=1)=[O:5].[CH:12]([Mg]Br)=[CH2:13]>O1CCCC1>[O:8]1[CH:9]=[CH:10][C:6]([C:4](=[O:5])[CH:12]=[CH2:13])=[N:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
The product of step (a) (0.66 g) was dissolved in dry tetrahydrofuran (20 ml), under a nitrogen atmosphere and cooled to −30° C. A solution of vinyl magnesium bromide (1M, 6 ml) was added dropwise over 5 minutes and the reaction mixture was allowed to warm to 0° C. and stirred at this temperature for 2 h. The mixture was then poured into ice-cold 2N hydrochloric acid (50 ml) and extracted into ethyl acetate. The extract was washed with water, brine, dried over magnesium sulphate and evaporated to give a dark oil (0.4 g).
Workup
- temperatureto warm to 0° C.
- extractionextracted into ethyl acetate
- washThe extract was washed with water, brine
- dry with materialdried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-8aba9f434020421a91c59b87e1b379e4
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887871B2
Reaction notes
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