Simple transformation of nitrile into ester by the use of chlorotrimethylsilane

Total Syntheses of Graphisin A and Sydowinin B

“…Similarly, treatment of 6 with methyl triflate in CH 2 Cl 2 followed by a methanolysis to access the imidate in a Ritter-type reaction was also unsuccessful. 15 Attempts to hydrolyze the nitrile in the presence of methanol (BF 3 , 16 FeCl 3 , 17 TMSCl, 18 and H 2 SO 4 19 ) resulted in mixtures of partially and fully MOM-deprotected compounds with the aryl nitrile remaining intact.…”

Tetrazolylhydrazides as Selective Fragment‐Like Inhibitors of the JumonjiC‐Domain‐Containing Histone Demethylase KDM4A

“…Pyridylacetohydrazides 11 d-f were synthesized by chlorinating the corresponding pyridylmethanols 13 a-c,f ollowed by Kolbe nitrile synthesis of the chloromethylpyridyl hydrochlorides 14 a-c [30] ands aponification of the resulting nitriles 15 a-c in the presence of as hort-chained alcohol to obtain esters 10 d-f,d irectly. [31] These esters were subsequently subjected to hydrazinolysis. Pyrazole and imidazole acetohydrazides 11 g and 11 h were obtained by alkylating the heterocycles with ethyl bromoacetate (16), followed by hydrazinolysis of intermediates 10 g and 10 h.…”

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

“…Nitriles are known to be metathesis catalyst poisons, therefore it was necessary to elaborate this group before testing the CM. Exposure of compound 33 to chlorotrimethylsilane in MeOH [31] provided the ester function with concomitant cleavage of the silyl ether due to the acidic conditions and afforded compound 34 in a good yield of 85 % over two steps. Oxidation with Dess-Martin periodinane followed by a chemoselective allylation using Barbier conditions gave the homoallylic alcohol 27, which upon exposure to TBSOTf in the presence of 2,6-lutidine provided the corresponding TBS ether in 81 % yield over the last three steps.…”