Reaktion #742075

Reaktionsgleichung

5-trimethylsilyl-3-furaldehyde

3-phenylpropylmagnesium bromide

1-bromo-3-phenylpropane

magnesium

sulfuric acid

→

alcohol

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

Lösungsmittel

ethyl ether

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0°
2. 2
   workup.ADDITIONpoured
3. 3
   SonstigeThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
4. 4
   WaschenThe organic portion was washed with water, saturated sodium chloride solution
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

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.

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