Triethylamine → Methyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylate

HRID 434028

Reaktionsgleichung

Reaktionsgleichung von HRID 434028
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=[N:6][OH:7])Cl.[CH3:12][O:13][C:14](=[O:18])[C:15]#[C:16][CH3:17].CCN(CC)CC>CCOCC>[CH3:12][O:13][C:14]([C:15]1[C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])=[N:6][O:7][C:16]=1[CH3:17])=[O:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 141019Methyl but-2-ynoateHCID 37581182-fluoro-N-hydroxybenzenecarboximidoyl chloride

Produkt 1

HCID 18756272Methyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a solution (0° C., N2) of 2-fluorobenzoylchloride oxime (0.50 g, 2.9 mmol) and methyl-2-butynoate (0.57 g, 5.8 mmol) in Et2O (15 ml) was added a solution of Et3N (0.52 ml) in Et2O (2 ml) over a period of 1 h followed by warming to room temperature while stirring overnight (17 h). The reaction was diluted with Et2O, washed (H2O then brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/EtOAc gradient) gave the title compound (0.39 g, 58%).

Aufarbeitung

  1. washwashed (H2O
  2. dry with materialbrine), dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8655af1fcd1c4c9a8078c341113f32f9
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670373B1

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