反应详情

4-Carbethoxy-5-methyl-2-vinyl-2,3-dihydrofuran was prepared using a phase transfer procedure similar to that of Example I. For the reaction, three grams tricaprylylmethylammonium chloride, 62 grams potassium hydroxide, and 100 mls sulfolane were charged to a reactor and a mixture of 65 grams ethyl acetoacetate and 95 grams 1,4-dichlorobutene-2 slowly added over a period of one hour while maintaining the temperature below 30° C. The mixture was then stirred for two hours at ambient temperature and then heated to 150° C. until the reaction was essentially complete. The reaction mixture was poured into ice-water, extracted with ether, and the ether evaporated using a rotary evaporator. The resulting product, which consisted of essentially a 1:1 mixture of 4-carbethoxy-5-methyl-2-vinyl-2,3-dihydrofuran and ethyl-1-acetyl-2-vinylcyclopropane-1-carboxylate, was distilled. Sixty grams of the 4-carbethoxy-5-methyl-2-vinyl-2,3-dihydrofuran obtained from the distillation was combined with 100 mls ethyl acetate and 0.4 grams supported hydrogenation catalyst (5% Pd on carbon) and hydrogenated in the usual manner. The catalyst was removed at the conclusion of the hydrogenation by filtration and ethyl acetate stripped under reduced pressure to obtain crude 4-carbethoxy-2-ethyl-5-methyl-2,3-dihydrofuran. Distillation of the crude product yielded essentially pure 4-carbethoxy-2-ethyl-5-methyl-2,3-dihydrofuran with chemical and physical properties and fragrance characteristics the same as described for the product of Example IX.

1. custom4-Carbethoxy-5-methyl-2-vinyl-2,3-dihydrofuran was prepared
2. additionwere charged to a reactor
3. additionslowly added over a period of one hour
4. temperaturewhile maintaining the temperature below 30° C
5. temperatureheated to 150° C. until the reaction
6. extractionextracted with ether
7. customthe ether evaporated
8. customa rotary evaporator
9. additiona 1:1 mixture of 4-carbethoxy-5-methyl-2-vinyl-2,3-dihydrofuran and ethyl-1-acetyl-2-vinylcyclopropane-1-carboxylate
10. distillationwas distilled