Реакция #44489

Уравнение реакции

solution

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

4-methylmorpholine N-oxide

→

title compound

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

Растворители

dichloromethane

Условия реакции

Обработка

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

Методика

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.

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