反応 #742101

反応方程式

3-furaldehyde

3-phenylpropyl magnesium bromide

iodine

1-bromo-3-phenylpropane

magnesium

sulfuric acid

→

alcohol

3-(1-Hydroxy-4-phenylbutyl)furan

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 bisulfite
4. 4
   洗浄The organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他to give an oil
9. 9
   その他This material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane)

実験手順

To a stirred solution of 3-phenylpropyl magnesium bromide (4.5 ml of a 2.73M solution in ethyl ether, 12.3 mmol, generated from 1-bromo-3-phenylpropane and magnesium and initiated with iodine) at 0° under argon, was added dropwise 3-furaldehyde (1.08 g., 11.2 mmol) in 5 ml ethyl ether. This solution was allowed to warm to room temperature, stirred for 20 minutes, and then poured over crushed ice containing several drops of concentrated sulfuric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bisulfite. The organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give an oil. This material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane) to give the desired alcohol.

出典