Reaktion #73717

Reaktionsgleichung

3

(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanol

→

(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 6 hr
2. 2
   FiltrationThe reaction mixture was filtered through Celite
3. 3
   Waschenthe filter cake was washed with ethyl acetate
4. 4
   SonstigeThe solvent was removed on a rotary evaporator
5. 5
   Sonstigethe crude product was purified by chromatography on silica (110 g) with 5% ethyl acetate in heptane (5 L)
6. 6
   Sonstigeto produce 4 (2.75 g, 64% over 2 steps)

Vorschrift

A solution of crude 3 (10.25 mmol) in dichloromethane (160 mL) was treated with manganese dioxide (14 g, 15 equiv.) and this suspension was stirred under reflux for 6 hr. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was removed on a rotary evaporator and the crude product was purified by chromatography on silica (110 g) with 5% ethyl acetate in heptane (5 L) to produce 4 (2.75 g, 64% over 2 steps).

Quelle