Reaktion #51519

Reaktionsgleichung

allyl bromide

Adenosine

P2O5

Sodium hydride

→

title compound

Ausbeute 66.0%

3′-O-allyl adenosine

Ausbeute 66.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDMF was removed under vacuum and residue
2. 2
   Waschenwas washed with ethyl acetate (100 mL)
3. 3
   SonstigeEthyl acetate layer was decanted
4. 4
   SonstigeFiltrate obtained
5. 5
   Wascheneluted with 10% MeOH in CH2Cl2

Vorschrift

Adenosine (20 g, 74.84 mmol) was dried over P2O5 under high vacuum at 40° C. for two days. It was then suspended in DMF under inert atmosphere. Sodium hydride (2.5 g, 74.84 mmol, 60% dispersion in mineral oil), stirred at room temperature for 10 minutes. Then allyl bromide (7.14 mL, 82.45 mmol) was added dropwise and the reaction mixture was stirred at room temperature overnight. DMF was removed under vacuum and residue was washed with ethyl acetate (100 mL). Ethyl acetate layer was decanted. Filtrate obtained contained product. It was then placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get the title compound (15.19 g, 66%). Rf 0.4, 0.4a ((10% MeOH in CH2Cl2)

Quelle