Réaction #44489

Équation de réaction

solution

5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanol

4-methylmorpholine N-oxide

→

title compound

5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanone

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred for another three hours
3. 3
   FiltrationThe black mixture was filtered through a pad of Celite
4. 4
   Autrethe solvent was evaporated
5. 5
   AutreThe residue was purified over silica gel using 5-50% ethyl acetate in hexanes

Mode opératoire

Tetrapropylammonium perruthenate (0.82 g, 2.43 mmol) was added to a stirred and cooled (0° C.) solution of Example 5A (12.11 g, 46.90 mmol), 4-methylmorpholine N-oxide (8.24 g, 70.35 mmol), and 4 Å molecular sieves (23 g) in dry dichloromethane (120 mL). After the addition, the mixture was warmed to room temperature and stirred for another three hours. The black mixture was filtered through a pad of Celite and the solvent was evaporated. The residue was purified over silica gel using 5-50% ethyl acetate in hexanes to give the title compound as an oil.

Source