Methyl acetoacetate → Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

HRID 2120855

Reaktionsgleichung

Reaktionsgleichung von HRID 2120855
[C:1](=[N:9][OH:10])(Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=O.C(N(CC)CC)C.C(OCC)(=O)C>C(O)C.C(Cl)Cl>[CH3:18][O:17][C:11]([C:12]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][O:10][C:13]=1[CH3:15])=[O:16]

Komponenten

7

Edukt 4

HCID 7757Methyl acetoacetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Produkt 1

HCID 727920Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

An ethanol solution of freshly prepared benzoyl chloride oxime (14.0 g, 90 mmol) (100 mL) was added dropwise, at 5° C. to methyl acetoacetate (11.18 g, 96 mmol) and triethyl amine (13 mL, 103 mmol) in ethanol (50 ml). After stirring for 12 hr at ambient temperature, the solution was diluted with CH2Cl2, washed with 1N HCl. saturated NaHCO3, brine, dried over MgSO4 and evaporated to give amber oil. Flash chromatography (silica) with 10% ethyl acetate in hexanes afforded the title compound (7.56 g, 39% yield) as a white solid: MS m/z MH+218 (100); 1H NMR (CDCl3) δ 2.78 (s, 3H), 3.81 (s, 3H), 7.45-7.55 (m, 3H), 7.65-7.69 (m, 2H).

Aufarbeitung

  1. washwashed with 1N HCl
  2. dry with materialsaturated NaHCO3, brine, dried over MgSO4
  3. customevaporated
  4. customto give amber oil

Quellen und Nachweise

ORD-Eintrag
ord-0c9ed052a79845ebb3fc2724cf6a8f4f
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693108B2

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