反応 #51519

反応方程式

allyl bromide

Adenosine

P2O5

Sodium hydride

→

title compound

収率 66.0%

3′-O-allyl adenosine

収率 66.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他DMF was removed under vacuum and residue
2. 2
   洗浄was washed with ethyl acetate (100 mL)
3. 3
   その他Ethyl acetate layer was decanted
4. 4
   その他Filtrate obtained
5. 5
   洗浄eluted with 10% MeOH in CH2Cl2

実験手順

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)

出典