Reaktion #454480

Reaktionsgleichung

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

potassium cyanide

water

→

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

Ausbeute 13.0%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   Extraktionextracted with ether
4. 4
   Waschenthe combined organic layers were washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by silica gel column chromatography
8. 8
   Wascheneluting with n-hexane containing 9-13% ethyl acetate

Vorschrift

In 5 ml of dimethyl sulfoxide were dissolved 1.00 g of 5-acetoxy-4,6-di-t-butyl-2-iodomethyl-2-methyl-2,3-dihydrobenzofuran synthesized in Example 70-2) and 0.36 g of potassium cyanide and the mixture was heated with stirring at 140° C. under nitrogen overnight. After cooling to room temperature, the reaction solution was poured into water and extracted with ether, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography eluting with n-hexane containing 9-13% ethyl acetate to give 0.09 g of 4,6-di-t-butyl-2-cyanomethyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a colorless solid (yield 13%).

Quelle