Triethylamine → 4-Ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole

HRID 434054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434054
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=[N:6][OH:7])Cl.[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].CCN(CC)CC>CCOCC>[CH2:13]([O:15][C:16]([C:17]1[C:4]([C:3]2[C:8]([F:12])=[CH:9][CH:10]=[CH:11][C:2]=2[I:1])=[N:6][O:7][C:18]=1[CH3:19])=[O:20])[CH3:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 591193512-Iodo-6-fluorobenzoyl chloride oxime

Produkt 1

HCID 227138064-Ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a solution of 2-iodo-6-fluorobenzoyl chloride oxime (26.6 mmol) and ethyl-2-butynoate (3.72 ml, 31.92 ml, 1.2 eq.) in Et2O (106 ml) under N2, stirring at 0-5° C. added dropwise a solution of Et3N (4.81 ml, 34.6 mmol, 1.3 eq) in Et2O (13 ml) over 1 h. The reaction was allowed to warm to room temperature and stirred overnight. Et2O was added and then washed with H2O, brine, dried (MgSO4), filtered, and concentrated. The crude residue was chromatographed on silica gel using ethyl acetate in hexanes (1-20%) to give the title compound (8.21 g, 82%).

Aufarbeitung

  1. washwashed with H2O, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0d84eef45a6b40cb9a73fbe4f691b8b0
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670373B1

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