Synthesis of 4-hydroxy-2,5-dimethylfuran-3(2H)-one (furaneol) from (2R,3R)-tartaric acid
作者:Mark A. Briggs、Alan H. Haines、Haydn F. Jones
DOI:10.1039/p19850000795
日期:——
(2R,3R)-Tartaric acid (6) has been converted through a five-step sequence into the important volatile flavour and aroma component 4-hydroxy-2,5-dimethylfuran-3(2H)-one (furaneol)(1) in 18.5% overall yield. The key step involves the formation of (4R,5R)-4,5-diacetyl-2,2-dimethyl-1,3-dioxolane (10) by reaction of methylmagnesium chloride with the corresponding 4,5-bis(dimethylamide). The same dioxolane
(2R,3R)-酒石酸(6)已通过五步转换成重要的挥发性风味和香气成分4-羟基-2,5-二甲基呋喃-3(2 H)-一(呋喃酚)(1),总收率为18.5%。关键步骤涉及通过氯化甲基镁与相应的4,5-双(二甲基酰胺)的反应形成(4 R,5 R)-4,5-二乙酰基-2,2-二甲基-1,3-二氧戊环(10) )。还通过涉及在相应的二腈上的格氏(Grignard)型反应的相关反应序列,也制备了相同的二氧戊环(10)。