Synthesis of trimethylsilyl carboxylates by HMDS under solvent-free conditions. Issue 37 (15th September 2016)

• Record Type: Journal Article
• Authors: Jereb, Marjan; Lakner, Janja
• Is Part Of: Tetrahedron. Volume 72:Issue 37(2016)
• Page Start: 5713
• Page End: 5723
• Publication Date: 2016-09-15
• Subjects: Carboxylic acids -- HMDS -- Trimethylsilyl carboxylates -- Solvent-free; BNAGIDDOEKUJRZ-UHFFFAOYSA-N -- PYFBRRMHOWLGJH-UHFFFAOYSA-N -- DLGMXYANUUYZRC-UHFFFAOYSA-N -- HSOHINBQIXUOBT-UHFFFAOYSA-N -- WWCXSUHALKENOU-UHFFFAOYSA-N -- TXRIDBWLZZFFPG-KRWDZBQOSA-N -- UUTZVQNCBBAIBO-UHFFFAOYSA-N -- XWDMNLMNKPTAHM-UHFFFAOYSA-N -- WTKBVIKDTAQSLT-UHFFFAOYSA-N -- KOBVFHOYKVSKPU-BQYQJAHWSA-N -- DOSHUJGCYZNXCI-UHFFFAOYSA-N -- MPTRXIJLGGCIEN-UHFFFAOYSA-N -- ARBMRXWJMMEFPM-UHFFFAOYSA-N -- LWBFIZBQVRDUMY-UHFFFAOYSA-N -- PPUSJGXNIQTKKU-UHFFFAOYSA-N -- SGSKFENRYUZSIQ-UHFFFAOYSA-N -- QXBLMUZEBBSOJH-UHFFFAOYSA-N -- ZOTLJAZLFPDMSU-UHFFFAOYSA-N -- QWDJSIANUZLFHV-UHFFFAOYSA-N -- BIKFDJNAMKPPRE-UHFFFAOYSA-N -- NTWRBVRZYOLGDK-UHFFFAOYSA-N -- DVGSOFSBBKDKRU-UHFFFAOYSA-N -- SYYAEMSUYPTHQI-AWEZNQCLSA-N -- NHWDOVCGDCJBOM-UHFFFAOYSA-N -- WDMPLKCIPYPEIM-UHFFFAOYSA-N -- APVNJYLNHAHELF-UHFFFAOYSA-N -- QWZYHXBREBIFEX-UHFFFAOYSA-N -- XURFXZGYZJXCEH-VQHVLOKHSA-N -- QGQNCTUAZAEYNK-UHFFFAOYSA-N -- PYJUBHQOZUNCIC-UHFFFAOYSA-N -- LNCMAONKWDVYSZ-UHFFFAOYSA-N -- JZIXRRXJQVBHJP-UHFFFAOYSA-N -- APACGNWFQWQPTA-UHFFFAOYSA-N -- SVUDYHRBVRXHLH-UHFFFAOYSA-N -- RBSGGNJKWHJKPQ-UHFFFAOYSA-N -- AHCNMCIDHXSNAK-UHFFFAOYSA-N -- JUZOFKLPPHUUMC-UHFFFAOYSA-N -- IQBYEIMLYYJKHK-UHFFFAOYSA-N -- XMEORGBWULGDAQ-UHFFFAOYSA-N -- GRONVOGSDOJOMG-UHFFFAOYSA-N -- QUUDZINXVRFXLB-UHFFFAOYSA-N -- FSVGZVHTOPZBGT-JTQLQIEISA-N -- IMXGFRQEUGCVTD-UHFFFAOYSA-N -- YUEDACRGSFFXGS-UHFFFAOYSA-N -- VOVIHULKTZBZND-UHFFFAOYSA-N -- YQVAQSPGNGFHAH-JXMROGBWSA-N -- FINLRQGHNQCJHK-UHFFFAOYSA-N -- FGTNBYWFNITQJR-UHFFFAOYSA-N -- GKODXEXJNJLBCA-UHFFFAOYSA-N -- XGABXNUFKZKQCO-UHFFFAOYSA-N -- PRHXXDHPUJYOBM-UHFFFAOYSA-N -- QSBLMZZLVMXTHB-UHFFFAOYSA-N -- MNAHHNNCUWYWKF-UHFFFAOYSA-N -- LCECHEBBTQXPPG-UHFFFAOYSA-N -- MJAVUGRHOBESSJ-UHFFFAOYSA-N -- KZAZJSUITNPGRM-UHFFFAOYSA-N -- XVQPISUQLXNRHH-UHFFFAOYSA-N -- ATCKJLDGNXGLAO-UHFFFAOYSA-N -- OIICSTDTKNOLJV-JTQLQIEISA-N -- AYGQUFGXOJWAHD-UHFFFAOYSA-N -- MFPKMKJUNGWICD-UHFFFAOYSA-N -- XVCXIVAVMFNKDH-UHFFFAOYSA-N -- HEVXLPBSUCJVAQ-MDZDMXLPSA-N -- MERYBIQYGCEFJY-UHFFFAOYSA-N -- GRHSLTISTCPPAT-UHFFFAOYSA-N -- DCFLHASZMCLJCP-UHFFFAOYSA-N -- VFFKJOXNCSJSAQ-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.08.003
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A broad set of structurally different carboxylic acids were transformed into their trimethylsilyl esters with HMDS in a practically completely solvent-free process, while a catalytic amount of iodine was required in some cases. The process has several advantages over the known methods: untreated reactants, air atmosphere, mild and neutral conditions, no evolution of hydrogen halide, no need of an additional base, low amount of waste, completely without chromatography, low consumption of energy, and operational simplicity. Graphical abstract: