Synthesis of (2,3-dihydrobenzofuran-3-yl)acetic acids from salicylic aldehydes: Trimethylsilyl as traceless activating group

被引：0
|
作者：
Buev, Evgeny M. [1 ]
Khardina, Polina A. [1 ]
Moshkin, Vladimir S. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia
来源：
TETRAHEDRON LETTERS | 2024年 / 152卷
关键词：
Dihydrobenzofurans; Traceless activating group; Trimethylsilyl (TMS) group; Acetic acids; Cyclization; ASYMMETRIC-SYNTHESIS; DIHYDROBENZOFURANS;
D O I：
10.1016/j.tetlet.2024.155354
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give the silylated ortho-methoxy benzaldehydes in 85-96 % yields. These aldehydes were converted into arylidenemalonates in excellent yields. O-(Trimethylsilyl)methyl group was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the alkene moiety promoted by cesium fluoride in DMF at 140 degrees C. In this way, (2,3-dihydrobenzofuran-3-yl)acetic acids and the corresponding esters were synthesized from salicylic aldehydes in 41-70 % overall yields.
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页数：4
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