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

HRID 1375632

Reaktionsgleichung

Reaktionsgleichung von HRID 1375632
[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-85ee4dd0ad78463d8ae1db24a55b2f05
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169798B2

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