Methyl acetoacetate → Methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate

HRID 1805265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805265
Cl[C:2](=[N:11][OH:12])[C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].C(N(C(C)C)CC)(C)C.O=[C:23]([CH3:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26]>>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=1[C:2]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH3:29])[O:12][N:11]=1

Komponenten

4

Edukt 3

HCID 7757Methyl acetoacetateHCID 81531DiisopropylethylamineHCID 28001642,6-Dichlorobenzaldchloroxime

Produkt 1

HCID 619436Methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylateAusbeute 87 %

Versuchsvorschrift

To a solution of 0.1 g (0.4455 mmol) alpha-Chloro-2,6-dichlorobenzaldoxime in 5 mL methyl 3-oxobutanoate, 0.11 mL (1.5 eq) diisopropylethlamine were added. The mixture was stirred for 24 h then ethylacetate was removed in the vacuo. The residue was dried under high vacuo and the crude product was triturated in water until it became solid. The solid was filtered off and further purified by recrystallization from a water-methanol mixture. The crystals were filtered off, washed with water and dried under reduced pressure to afford 248 mg (87%) of methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate. Result of LC/MS [M+H]+: 286.12; 1H NMR (DMSO-d6; CCl4): 2.77 (3H, s, CH3-isooxazole), 3.28 (3H, s, CH3-methoxy), 7.54-7.65 (3H, m, aromatic)

Aufarbeitung

  1. customethylacetate was removed in the vacuo
  2. customThe residue was dried under high vacuo
  3. customthe crude product was triturated in water until it
  4. filtrationThe solid was filtered off
  5. customfurther purified by recrystallization from a water-methanol mixture
  6. filtrationThe crystals were filtered off
  7. washwashed with water
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8a28c3e898c4ffd88a5bd5a2a6ff565
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354436B2

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