Water → 3-(5-Hexenyl)-1-methylthymine

HRID 129888

Reaktionsgleichung

Reaktionsgleichung von HRID 129888
[H-].[Na+].[CH3:3][N:4]1[CH:12]=[C:10]([CH3:11])[C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O>CS(C)=O>[CH2:19]([N:7]1[C:8](=[O:9])[C:10]([CH3:11])=[CH:12][N:4]([CH3:3])[C:5]1=[O:6])[CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedione

Produkt 1

HCID 232959493-(5-Hexenyl)-1-methylthymineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of sodium hydride (343 mg, 14 mmol) and 1-methylthymine (2.00 g, 14 mmol) in dimethylsulfoxide (30 ml) was stirred for 15 minutes, and then 6-bromo-1-hexene (2.30 g, 14 mmol) was added. After stirring for 69 hours, the reaction mixture was poured into water (100 ml) and extracted with dichloromethane (4×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (40 ml), dried over sodium sulfate, and then the solvent was evaporated under vacuum to give a residue which was recrystallized (dichloromethane-ethyl ether) to give 3-(5-hexenyl)-1-methylthymine (2.80 g, 88% yield).

Aufarbeitung

  1. stirringAfter stirring for 69 hours
  2. extractionextracted with dichloromethane (4×50 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (40 ml)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customto give a residue which
  7. customwas recrystallized (dichloromethane-ethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-3a8a964712514c0a8126c1115ee06d0f
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470878

Verknüpfte Notizen

Wird geladen…