Triethylamine → Methyl 3-phenyl-4-isoxazolecarboxylate

HRID 83417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83417
[OH:1]/[N:2]=[C:3](\Cl)/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][O:12][C:13](/[CH:15]=[CH:16]/OC(=O)C1C=CC([N+]([O-])=O)=CC=1)=[O:14].C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]([C:15]1[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:2][O:1][CH:16]=1)=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5706359Alpha-chlorobenzaldoximeHCID 5706833[(E)-3-methoxy-3-oxoprop-1-enyl] 4-nitrobenzoate

Produkt 1

HCID 10750662Methyl 3-phenyl-4-isoxazolecarboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of (E)- and/or (Z)—N-hydroxy-benzenecarboximidoyl chloride (12.0 g, 77 mmol) and 4-nitro-benzoic-acid (E)-2-methoxycarbonyl-vinyl ester (9.7 g, 39 mmol) in dichloromethane (200 mL) was added triethylamine (20.9 mL, 150 mml) and the resulting solution stirred overnight at room temperature. The mixture was then diluted with dichloromethane (500 mL) and the organic extract removed and washed with water, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title product (3.1 g, 40%) which was obtained as a light yellow oil. MS: m/e=204.2 [M+H]+

Aufarbeitung

  1. extractionthe organic extract
  2. customremoved
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4b74dbc3553e47268ddb75d7569663ba
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846719B2

Notizen zur Reaktion

Wird geladen…