Reacción #51519

Ecuación de reacción

allyl bromide

Adenosine

P2O5

Sodium hydride

→

title compound

Rendimiento 66.0%

3′-O-allyl adenosine

Rendimiento 66.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroDMF was removed under vacuum and residue
2. 2
   Lavadowas washed with ethyl acetate (100 mL)
3. 3
   OtroEthyl acetate layer was decanted
4. 4
   OtroFiltrate obtained
5. 5
   Lavadoeluted with 10% MeOH in CH2Cl2

Procedimiento

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)

Fuente