引用本文:
张合胜, William Kitching. 2,8-二甲基-1,7-二氧杂螺[5,5]十一烷的合成[J]. 应用化学,
2002, 19(4): 404-406.
Citation: ZHANG He-Sheng, William Kitching. Synthesis of 2,8-Dimethyl-1,7-dioxaspiroundecane[J]. Chinese Journal of Applied Chemistry, 2002, 19(4): 404-406.
Citation: ZHANG He-Sheng, William Kitching. Synthesis of 2,8-Dimethyl-1,7-dioxaspiroundecane[J]. Chinese Journal of Applied Chemistry, 2002, 19(4): 404-406.
English
Synthesis of 2,8-Dimethyl-1,7-dioxaspiroundecane
Abstract:
Alkylation of diethyl 3-oxoglutarate monoanion by 4-bromobutene to produce enone diester 3, subsequent alkylation of 3 with 4-bromo-1-butene using K2CO3 and a catalytic amount of NaIin the mixed solvent afforded dienone diester 4, which underwent decarboxylative hydrolysis when treated with 15% KOH in methanol under refluxing to provide dienone 5. The dienone afforded 2,8-dimethyl-1,7-dioxaspiroundecane 1 in good yield and high purity via an oxymercuration-cyclisation-reduction sequence.
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Key words:
- spiroketal
- / fruit fly pheromone
- / synthesis
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