Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine
نویسندگان
چکیده
2-Benzyloxy-1-methylpyridinium triflate (1) is emerging as a mild, convenient, and in some cases uniquely effective new reagent for the synthesis of benzyl ethers and esters. This article provides a revised benzyl transfer protocol in which N-methylation of 2-benzyloxypyridine delivers the active reagent in situ. Observations on the appropriate choice of solvent (toluene vs. trifluorotoluene) and the extension of this methodology to the synthesis of other arylmethyl ethers are included.
منابع مشابه
CLEAVAGE OF ESTERS AND ETHERS WITH SILICA CHLORIDE
Silica chloride converted benzyl or tert-butyl esters to the corresponding acid chlorides and alkyl chlorides. It also converted benzyl or tert-butyl phenyl ethers to the corresponding allcyl chlorides and phenol
متن کاملPhotochemical heterolysis of 3,5-bis(dimethylamino)benzyl alcohols and esters: generation of a benzyl cation with a low-energy triplet state.
An earlier computational study (CASPT2/pVDZ) by Winter et al. predicts the 3,5-bis(dimethylamino)benzyl cation to have nearly degenerate singlet and triplet states. Through product studies it is demonstrated that photolysis of 3,5-bis(dimethylamino)benzyl alcohol and its corresponding acetate and phenylacetate esters in alcoholic solvents produces a solvent incorporated adduct, 3,5-bis(dimethyl...
متن کاملAccessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This B-N isostere has been shown to...
متن کاملDeprotection of Benzyl and t-Butyl Phosphate, Phosphite, and Sulfite Esters by Silica Chloride
Deprotection of phosphate, phosphate, and sulfite esters by silica chloride is described. Silica chloride is a mild, selective, and effective reagent for cleavage of benzyl and t-butyl esters of the above compounds.
متن کاملStereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides.
Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA-acetonitrile-toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Beilstein Journal of Organic Chemistry
دوره 4 شماره
صفحات -
تاریخ انتشار 2008