반응 #742101

반응 방정식

3-furaldehyde

3-phenylpropyl magnesium bromide

iodine

1-bromo-3-phenylpropane

magnesium

sulfuric acid

→

alcohol

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

용매

ethyl ether

ethyl ether

반응 조건

후처리

1. 1
   기타at 0°
2. 2
   workup.ADDITIONpoured
3. 3
   기타The resulting mixture was partitioned between ethyl ether and 5% sodium bisulfite
4. 4
   세척The organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to give an oil
9. 9
   기타This material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane)

실험 절차

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.

출처