5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-2-PENTENAL synthesis

Yield:-

Reaction Conditions:

Stage #1: diiodomethane;diethylzinc in hexane;1,2-dichloro-ethane; for 1.5 h;
Stage #2: (E/Z)-3,7-dimethyl-2,6-octadienal in hexane;1,2-dichloro-ethane at 20;

Steps:

1

To an oven dried 50OmL round bottomed flask was added 1 ,2-dichloroethane (85mL) under a nitrogen atmosphere. Diethylzinc (3OmL, IM in hexanes) was added, and then diiodomethane (15g) was introduced dropwise over 1 hour. Following stirring for 30 minutes (a white precipitate formed) citral (l .lg) was added and the reaction was stirred overnight at room temperature.The reaction mixture was poured into a potassium carbonate solution (10OmL, 20%) and then filtered through a pad of Celite in a sintered funnel. The organic layer was separated and dried over sodium sulfate. Filtration of the drying agent, concentration and flash column chromatography with dichloromethane as eluent gave the title compound.

References:

WO2006/69224,2006,A2 Location in patent:Page/Page column 22