Réaction #452443

Équation de réaction

linalool

Diketene

→

desired product

Rendement 92.0%

3,7-dimethyl-1,6-octadien-3-yl 3-oxo-butyrate

Rendement 92.0%

Conditions de réaction

Traitement

1. 1
   Autrefitted with a condenser, argon inlet, addition funnel, magnetic stirrer
2. 2
   Températurethe mixture is cooled to room temperature
3. 3
   AutrePurification of an earlier sample from this route
4. 4
   Lavageby flash chromatography (elution with dichloromethane)

Mode opératoire

A mixture of linalool (100 g, 0.648 mol) and 4-dimethylaminopyridine (0.40 g, 3.20 mmol) in a 500 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, addition funnel, magnetic stirrer and internal thermometer is heated to 55° C. Diketene (54.50 g, 0.648 mol) is added dropwise in the course of 30 min. The mixture has a slight exotherm and turns from yellow to red during this time. After stirring an additional hour at 50° C., the mixture is cooled to room temperature. At this point, NMR analysis indicates the reaction is complete. The material from this lot is carried onto the next step. Purification of an earlier sample from this route by flash chromatography (elution with dichloromethane) yields the desired product in 92% yield and nearly colorless.

Source