Reaktion #74432

Reaktionsgleichung

(1R,2S,4R,5S)-5-(tert butyldiphenylsilyloxy)-bicyclo[2.2.1]heptan-2-ol

Pyridinium chlorochromate

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title compound

(1R,4R,5S)-5-(tert-Butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-one

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was gradually warmed to ambient temperature
2. 2
   Filtrationfiltered through a pad of silica gel
3. 3
   SonstigeRemoval of the solvents

Vorschrift

Silica gel 60 (particle size, 0.040-0.063 mm, CAS # 63231-67-4, from EMD Chemical Inc., 21 g) was added to a solution of (1R,2S,4R,5S)-5-(tert butyldiphenylsilyloxy)-bicyclo[2.2.1]heptan-2-ol (6.75 g, 18.4 mmol) in anhydrous dichloromethane (100 mL). The mixture was cooled to 0° C. Pyridinium chlorochromate (6.35 g, 29.5 mmol) was added to the mixture. The reaction mixture was gradually warmed to ambient temperature and stirred at this temperature for 16 h. The mixture was diluted with dichloromethane, and filtered through a pad of silica gel. Removal of the solvents gave the title compound as a colorless viscous oil.

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