Reaction #742101

Reaction equation

3-furaldehyde

3-phenylpropyl magnesium bromide

iodine

1-bromo-3-phenylpropane

magnesium

sulfuric acid

→

alcohol

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

Solvents

ethyl ether

ethyl ether

Conditions

Workup

1. 1
   Otherat 0°
2. 2
   workup.ADDITIONpoured
3. 3
   OtherThe resulting mixture was partitioned between ethyl ether and 5% sodium bisulfite
4. 4
   WashThe organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   Otherto give an oil
9. 9
   OtherThis material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane)

Procedure

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.

Source