o-Fluorostyrene → 2-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH2:5].C(=O)(O)[O-].[Na+].[Cl:15][CH2:16][C:17](=[O:22])[C:18](Cl)=[N:19][OH:20]>C1(C)C=CC=CC=1>[Cl:15][CH2:16][C:17]([C:18]1[CH2:5][CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])[O:20][N:19]=1)=[O:22]Participants
5
Conditions
- Temperature
- 55 °C
Procedure
To a suspension of 2-fluorostyrene (2.78 g, 22.8 mmol) and sodium bicarbonate (2.88 g, 34.2 mmol) in anhydrous toluene (15 mL) heated at 55° C. was added 3-chloro-N-hydroxy-2-oxo-propanimidoyl chloride (1.78 g, 11.4 mmol). After 2 h at 55° C., the reaction mixture was cooled, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as eluant to provide the title compound as a yellow solid (2.35 g) melting at 42-44° C.
Workup
- temperaturethe reaction mixture was cooled
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe resulting residue was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as eluant
Sources & evidence
- ORD record
- ord-b1c43041b0794deda4cc88c6e014edc5
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349870B2
Reaction notes
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