Diethyl Ether → HCID 89739088, compound

Participants

Reaction Steps

(E)-5-cyclohexyl-2,4-dimethylpent-4-enal (2.18 g; 11 mmol) was hydrogenated at 20 bar and room temperature in cyclohexane (20 ml) in the presence of 5% w/w palladium on charcoal (0.18 g). The thus obtained crude product was dissolved in dry dichloromethane (20 ml) and added drop-wise to a mixture of anhydrous sodium acetate (5 g) and finely ground pyridinium chlorochromate (PCC; 4.84 g; 22 mmol) in dry dichloromethane (50 ml) at 0° C. under nitrogen. The reaction was then stirred for 2 hours at room temperature. Diethyl ether (400 ml) was added to the reaction. After stirring for 30 minutes, the reaction was filtered through a short pad of silica gel, rinsing with diethyl ether. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 20:1) followed by bulb-to-bulb distillation (60° C./0.1 mbar). The product was obtained with a yield of 51% as a mixture of diastereoisomers.

Provenance & Evidence