反応 #742075

反応方程式

5-trimethylsilyl-3-furaldehyde

3-phenylpropylmagnesium bromide

1-bromo-3-phenylpropane

magnesium

sulfuric acid

→

alcohol

4-(1-Hydroxy-4-phenylbutyl)-2-trimethylsilylfuran

溶媒

ethyl ether

ethyl ether

反応条件

後処理

1. 1
   その他at 0°
2. 2
   workup.ADDITIONpoured
3. 3
   その他The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
4. 4
   洗浄The organic portion was washed with water, saturated sodium chloride solution
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated

実験手順

To a stirred solution of 3-phenylpropylmagnesium bromide (3.3 ml of an 0.313M solution in ethyl ether, 1.03 mmol, generated from 1-bromo-3-phenylpropane and magnesium) at 0° under argon, was added dropwise 5-trimethylsilyl-3-furaldehyde (0.145 g., 0.862 mmol) in 5 ml ethyl ether. This solution was allowed to warm to room temperature, stirred for one hour, and then poured over crushed ice containing several drops of concentrated sulfuric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol.

出典