Réaction #76382

Équation de réaction

(4-pentyl-cyclohexyl)-methanol

(4-Pentyl-cyclohexyl)-methanol

potassium carbonate

sodium periodate

2-Propanol

→

4-pentyl-cyclohexanecarboxaldehyde

Rendement 83.0%

4-Pentyl-cyclohexanecarboxaldehyde

Rendement 83.0%

Solvants

chloroform water

ruthenium chloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture was stirred for another 30 min at 60 C
2. 2
   Filtrationfiltered through celite
3. 3
   Extractionextracted with dichloromethane
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutrePurification by chromatography on silica gel (dichloromethane)

Mode opératoire

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%).

Source