کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5228794 1383643 2007 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Studies on a three-step preparation of β-fluoroalkyl acrylates from fluoroacetic esters
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Studies on a three-step preparation of β-fluoroalkyl acrylates from fluoroacetic esters
چکیده انگلیسی

β-Fluoroalkyl-acrylic esters are valuable building blocks for the synthesis of organofluorine compounds. Although the preparation of several β-fluoroalkyl-acrylates is known, a general and straightforward lab-scale methodology for the preparation of multigram amounts of these compounds from fluoroacetic esters is not available, and the related chemistry has not been investigated in detail. We now describe an optimized three-step protocol relying on: (1) Claisen-type condensation of fluoroacetic esters with ethyl acetate, using LDA as base; (2) reduction of the resulting γ-fluoro-β-keto esters by NaBH4, using toluene or benzene as solvents; (3) P2O5-promoted dehydration of the intermediate γ-fluoro-β-hydroxy esters. The methodology affords preparatively useful yields of the target compounds incorporating only fluorine atoms (CF3, CHF2, C2F5), whereas the γ-halodifluoromethyl (CClF2, CBrF2, CIF2) acrylates could not be obtained in analytically pure form from the dehydration step.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 63, Issue 9, 26 February 2007, Pages 2042-2046
نویسندگان
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