Реакция #76382

Уравнение реакции

(4-pentyl-cyclohexyl)-methanol

(4-Pentyl-cyclohexyl)-methanol

potassium carbonate

sodium periodate

2-Propanol

→

4-pentyl-cyclohexanecarboxaldehyde

Выход 83.0%

4-Pentyl-cyclohexanecarboxaldehyde

Выход 83.0%

Растворители

chloroform water

ruthenium chloride

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture was stirred for another 30 min at 60 C
2. 2
   Фильтрацияfiltered through celite
3. 3
   Экстракцияextracted with dichloromethane
4. 4
   Сушкаdried over MgSO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеPurification by chromatography on silica gel (dichloromethane)

Методика

To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%).

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