ethyl 2-(N-methyleneamino)-2-methylpropanoate → ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoate

HRID 1003154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003154
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:17])O[C:11](C)(C)[O:12][C:13]=1[CH3:14].C=[N:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:17])[N:19]([C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][O:12][C:13]=1[CH3:14]

Komponenten

4

Edukt 2

HCID 10855576ethyl 2-(N-methyleneamino)-2-methylpropanoateHCID 153008465-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one

Produkt 1

HCID 86755276ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoateAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 5-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one (2.0 g) and ethyl 2-(N-methyleneamino)-2-methylpropionate (1.45 g) was heated under reflux in xylene for 10 hours. After evaporation to dryness the residue was purified by dry column chromatography on silica gel eluting with cyclohexane/ethyl acetate to give ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoate as a pale yellow oil (1.7 g), NMR 1.24(t,3H), 1.42(s,6H), 1.57(s,3H), 4.15(q,2H), 5.3(s,2H), 7. 74(m,4H).

Aufarbeitung

  1. temperaturewas heated
  2. customAfter evaporation to dryness the residue
  3. customwas purified
  4. dry with materialby dry column chromatography on silica gel eluting with cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-086c87bfb705496487e718d7a6ebca51
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046135

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