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13th September 2011 @ 08:31
Hazard and Risk Assessment:[data]1386[/data] ProcedureTo a mixture of formaldehyde solution (0.21 ml, 2.33 mmol), 2,2-dimethoxyethylamine (0.34 mL, 2.33 mmol) and cyclohexanecarboxylic acid (300 mg, 2.33 mmol) in methanol (1.5 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (0.56 mL, 2.33 mmol) and stirred at room temperature for 24 h. EtOAc (5 mL) was then added to the reaction and was washed with 1 M HCl (5 mL), sat. NaCO3 solution (5mL) and brine (5 mL), dried over MgSO4, filtered and concentrated. A highly viscous orange-brown oil was obtained which was purified by column chromatography (silica gel, EtOAc/Hexane 75-100%) to give the product as clear oil 0.941 g, 2.0 mmol, 63% * formaldehyde solution was used rather than paraformaldehyde. The exact concentration of the solution was unclear. Also the wrong density was used for MNR4-1 was used as has not been determined. Therefore, two areas where stoichiometry errors have more than likely occurred. Column frac 5-14 clear oil LCMS [data]1486[/data] observed peaks rt 19.917-20.333 419 hemiaminal+H 487 M+H rt 20.683-21.317 415 unknown C22H28N2O5+H similar to LCMS of MW40 where hemiaminal+H (405) and M+Na (459) [data]1488[/data] 1H NMR MNR8-1contains the same impurities as MW40 LRMS [data]5343[/data] HRMS [data]5345[/data] Lab book page complete, MNR
Attached Files
MNR8-1 scheme.png
MNR8-1 table.PNG
LCMS MW40-1 starting material for MW56-3.pdf
7d LRMS MNR8-1 dont include.jpg
7d HRMS MNR8-1.jpg