After a quick peek there seems to be a lot of white solids in the now yellow NaBH4 post reaction mixture (could be all borate salts ofcourse but that is doubtfull). The mixture shouldnt have left sitting there like that
The starting 3,4,5-trimethoxynitrostyrene that was used had been recrystalized twice and gave a sharp mp of 118-119 °C.
One hour after the addition of the nitrostyrene the alcohol/water solution was milky white.
The yellow oil obtained from previous NaBH4 reductions of 3,4,5-trimethoxynitrostyrene (10 mmol runs) gave upon reduction of the nitro group using zinc/formic acid or zinc/potassium formate a wide variety of yields ranging from excellent to none.
Would anyone know what a good TLC solvent system would bee for 3,4,5-trimethoxynitrostyrene/3,4,5-trimethoxyphenylnitroethane?