Reaktion #454475

Reaktionsgleichung

hydrochloric acid

5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran

lithium aluminum hydride

Ethyl acetate

→

4,6-di-t-butyl-5-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran

Ausbeute 73.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   Sonstigethe concentrate was purified by silica gel column chromatography
7. 7
   Wascheneluting with n-hexane containing 20% ethyl acetate

Vorschrift

Under a nitrogen atmosphere, a solution of 500 mg of 5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 7 ml of tetrahydrofuran was added dropwise to a suspension of 114 mg of lithium aluminum hydride in 3 ml of tetrahydrofuran. The mixture was heated under reflux for 2 hours and then cooled to room temperature. Ethyl acetate was added dropwise and then 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated, and the concentrate was purified by silica gel column chromatography eluting with n-hexane containing 20% ethyl acetate to give 320 mg of 4,6-di-t-butyl-5-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran as a white solid (yield 73%).

Quelle