Reaktion #2392618

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 reaction mixture was heated
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   Sonstigeto attain room temperature
4. 4
   Extraktionthe mixture was extracted with ethyl acetate
5. 5
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane)

Vorschrift

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 under nitrogen atmosphere. The reaction mixture was heated under reflux for 2 hours. After allowing the mixture to attain room temperature, ethyl acetate was added dropwise, 10% hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane) to yield 320 mg (73%) of 4,6-di-t-butyl-5-hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran as a white solid.

Quelle