BarCharts QuickStudy Organic Chemistry Fundamentals by Inc. BarCharts

By Inc. BarCharts

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The ether is removed from the filtrate, and the residue is filtered to remove a small amount of the remaining precipitates. The filtrate is then distilled to give the corresponding esters of the carboxylic acid. The Mitsunobu reaction has found numerous applications. For instance, benzylic and styryl alcohols are esterified selectively in the presence of (poly)phenolics [199]. Otherwise difficult-to-achieve esterification of benzoic acids with phenols is feasible [200]. Inversion of sterically hindered 17-hydroxy steroids [201] and regioselective esterification of sucrose [202] are feasible.

5 GP) effects smooth esterification of monomethylsuccinates with tertiary alcohols [184]. 4-(Pyrrolidin-1-yl)pyridine is also a useful base for deconjugative coupling of 2-cyclohexylideneacetic acid [185]. 4 mmol with glycerol) is added to a stirred solution of carboxylic acid (10 mmol) in anhydrous CH2Cl2 (10 mL, DMF in case of sparingly soluble acids). DCC is added at 0 °C to the reaction mixture, which is then stirred for 5 min at 0 °C and 3 h at 20 °C. Precipitated urea is then filtered off and the filtrate is evaporated in vacuo.

The reaction is not sensitive to steric bulk of the reactants, allowing production of esters of tertiary alcohols. As such, a wide range of applications have been achieved in the fields of natural products, peptides, nucleotides, etc. The application of the DCC method in pure organic synthesis dates back to 1967 [178]. 25). 25 This original procedure, however, unfortunately suffers from some drawbacks: yields are not always high, and undesirable N-acylureas are occasionally formed. These drawbacks can be overcome by addition of strong acid such as ptoluenesulfonic acid [179, 180].

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