Triethylamine → 4-Methoxycarbonyl-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole

HRID 434033

Reaktionsgleichung

Reaktionsgleichung von HRID 434033
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=[N:6][OH:7])Cl.[CH3:13][O:14][C:15](=[O:24])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>CCOCC.O>[CH3:13][O:14][C:15]([C:16]1[C:4]([C:3]2[C:8]([F:12])=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])=[N:6][O:7][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 138378Phenylpropynoic acid methyl esterHCID 71367044HCID 71367044, Verbindung

Produkt 1

HCID 187562824-Methoxycarbonyl-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazoleAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a solution of 2-chloro-6-fluorobenzoylchloride oxime (1.04 g, 5.00 mmol) and methyl-3-phenyl-2-propynoate (1.20 g, 7.50 mmol) in Et2O (25 ml) at 0° C. under nitrogen was added a solution of triethyl amine (0.834 ml, 6.00 mmol) in Et2O (3 ml) over 1 h. The reaction was allowed to warm to room temperature overnight (17 h). The mixture was diluted with Et2O and H2O, the layers separated, and the organic fraction was dried (MgSO4). Column chromatography (silica gel, hexane/Et2O gradient) gave the title compound (1.53 g, 92%).

Aufarbeitung

  1. customthe layers separated
  2. dry with materialthe organic fraction was dried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-438d114149954189898f47939d083395
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670373B1

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