Dimethylformamide → Benzonitrile, 4-chloro-, N-oxide
Reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[Cl:8][C:9]1[CH:14]=[CH:13]C=[CH:11][CH:10]=1.CN(C)C=[O:18]>>[Cl:8][C:9]1[CH:14]=[CH:13][C:7]([C:6]#[N+:3][O-:18])=[CH:11][CH:10]=1Participants
Procedure
3.57 g (37 mmol) of triethylamine in 30 ml of dry dimethylformamide were added during 10 minutes while stirring and cooling at 10° C. to a solution of 6.33 g (33.3 mmol) of 4-chlorobenzene N-hydroxycarboximidoyl chloride in 60 ml of dry dimethylformamide. After 1 hour at 20° C. the solution of 4-chlorobenzonitrile oxide formed was poured into water and filtered off. The moist solid was dissolved in 150 ml of diethyl ether and dried twice with 10 g of molecular sieve (3A) each time. The ethereal solution was filtered and there were added thereto at 5° C. 6.56 g (36.6 mmol) of methyl 2-propynyloxy-2-methylpropionate in 25 ml of diethyl ether. After 24 hours the ether was removed and the product was purified by column chromatography on 220 g of silica gel using hexane/ethyl acetate (4:1) and then hexane/ethyl acetate (2:1) for the elution. There were obtained 4.67 g of methyl 2-[[3-(4-chlorophenyl)-5-isoxazolyl]methoxy]-2-methylpropionate in the form of a colourless oil having a purity of 99% according to high pressure liquid chromatography.
Sources & evidence
- ORD record
- ord-1a08bc8841d148a39670be290434e127
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04774253
Reaction notes
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