Reaktion #2273481

Reaktionsgleichung

5-acetoxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran

lithium aluminium hydride

→

5-hydroxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran

Ausbeute 64.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to 0° C.
2. 2
   Sonstigethe reaction was quenched with water
3. 3
   Extraktionthe reaction mixture was extracted with a 10% aqueous hydrochloric acid solution and ethyl acetate
4. 4
   WaschenThe organic layers were washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Vorschrift

Under argon atmosphere, 77 mg of 5-acetoxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran was dissolved in 1 ml of anhydrous tetrahydrofuran, a solution of 25 mg of lithium aluminium hydride in 2 ml of anhydrous tetrahydrofuran was added, and the solution was stirred at room temperature for a whole day and night. After cooling to 0° C., the reaction was quenched with water and then the reaction mixture was extracted with a 10% aqueous hydrochloric acid solution and ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate) to give 42 mg of 5-hydroxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran as a light red solid (yield 64%).

Quelle