Реакция #9328

Уравнение реакции

4-methylmorpholine N-oxide

1-3

(1-Propyl-cyclobutyl)-methanol

1-3

(1-Propyl-cyclobutyl)-methanol

→

1-4

1-Propyl-cyclobutanecarbaldehyde

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   Фильтрацияthe mixture was filtered through a pad of silica gel (dichloromethane)
4. 4
   Другоеthe dichloromethane was evaporated
5. 5
   workup.DISTILLATIONthe combined product was purified by distillation under reduced pressure

Методика

An ice-cold mixture of 4-methylmorpholine N-oxide (NMO) (1.683 g, 14.4 mmol), 1-3 (1.229 g, 9.59 mmol) and 4 Å molecular sieves (5.5 g) in dichloromethane (20 mL) was treated with tetrapropylammonium perruthenate (TPAP) (179 mg, 0.51 mmol). The mixture was stirred at 0° C. for 5 min. and then was allowed to warm to room temperature. After 1 h, the mixture was filtered through a pad of silica gel (dichloromethane) and the dichloromethane was evaporated. The crude product was combined with the crude product from another batch (starting with 4.986 g, 38.9 mmol of 1-3) and the combined product was purified by distillation under reduced pressure followed by flash chromatography on silica gel (15% ether/pentane) to give 1-4 (2.649 g, 43%).

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