Ethyl Acetoacetate → 3-Allyl-6-methyluracil

HRID 349288

Reaktionsgleichung

Reaktionsgleichung von HRID 349288
[CH2:1]([NH:4][C:5]([NH2:7])=[O:6])[CH:2]=[CH2:3].[C:8](OCC)(=[O:13])[CH2:9][C:10]([CH3:12])=O.[OH-].[K+]>C(O)C.Cl.CO>[CH2:1]([N:4]1[C:8](=[O:13])[CH:9]=[C:10]([CH3:12])[NH:7][C:5]1=[O:6])[CH:2]=[CH2:3]

Komponenten

7

Edukt 3

HCID 8868Ethyl AcetoacetateHCID 11181AllylureaHCID 14797Potassium Hydroxide

Produkt 1

HCID 136020473-Allyl-6-methyluracil

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To allylurea (25 g, 0.25 mol) in ethanol (10 mL) was added ethyl acetoacetate (31.86 mL, 0.25 mol) and 10 drops conc. HCl. After 12 days at room temperature, concentration gave an oil which was dissolved in MeOH. KOH (22.5 g, 0.34 mol) was added and the solution refluxed for 1 hour. After neutralization, the resulting solid 1 was collected. Yield 2.7 g (7%). NMR (CDCl3) δ: 2.16 (3H, s), 4.52 (2H, d), 5.18 (1H, d), 5.23 (1H, d), 5.60 (1H, s), 5.82–5.93 (1H, m), 10.3 (1H, s).

Aufarbeitung

  1. concentrationconcentration
  2. customgave an oil which
  3. temperaturethe solution refluxed for 1 hour
  4. customAfter neutralization, the resulting solid 1 was collected

Quellen und Nachweise

ORD-Eintrag
ord-07db849e044840039386e1356153d402
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179815B2

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