反応 #312575

反応方程式

4-Fluoro-4′-methoxy-benzophenone

4-fluoro-4′-methoxy-benzophenone

acetylene

Sodium acetylide

→

1-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol

溶媒

反応条件

後処理

1. 1
   その他separated
2. 2
   抽出the aqueous layer was extracted with three portions of diethyl ether (200 mL)
3. 3
   洗浄washed with saturated aqueous NH4Cl (200 mL), saturated aqueous NaCl (200 mL), and saturated aqueous sodium bicarbonate (200 mL)
4. 4
   乾燥The organic layer was dried over anhydrous sodium sulfate
5. 5
   その他evaporated to an amber colored oil

実験手順

4-Fluoro-4′-methoxy-benzophenone from Step 1 (126.7 grams) and acetylene saturated N,N-dimethylformamide (380 mL) were combined in a reaction flask. Sodium acetylide solution (9 weight % in toluene, 343 grams) was added to the reaction mixture dropwise over 45 minutes. The reaction mixture was stirred at room temperature for 1 hour and then poured into ice water (600 mL). The layers were phase separated and the aqueous layer was extracted with three portions of diethyl ether (200 mL). The organic layers were combined and washed with saturated aqueous NH4Cl (200 mL), saturated aqueous NaCl (200 mL), and saturated aqueous sodium bicarbonate (200 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to an amber colored oil yielding 136.6 grams of 1-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol. This material was not purified further but was used directly in the next step.

出典