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18th May 2012 @ 04:05
MNR13-2%20scheme.png

KAB5-1 (0.54 g, 1.33 mmol) in toluene (7 mL) was treated with methanesulfonic acid (0.09 mL, 1.33 mmol) and the reaction was stirred at room temperature for 5 hours by which time TLC had shown complete consumption of SM. The reaction was neutralised with sat. sodium hydrogen carbonate solution, the organic fraction extracted and the aqueous fraction was washed with EtOAc (10 mL x 3). The organic layers were combined, dried, filtered and concentrated to give a dark brown oil.

TLC after 5 hours in 100% EtOAc
MNR13-2 5 hours


Crude - 0.473 g

Column 30-100% EtOAc/Hex

Frac 9-20 0.125 g, 0.40 mmol, 30 % as MNR13-2-INT

MNR13-2-INT.png

mnr13-2_frac9-20_1H.pdf


Other fractions collected 0.141 g - messy NMR

mnr13-2_other fractions_1H.pdf


Total mass recovered 0.266 g - very poor based on the crude recovered. This reaction was not expected to yield starting material but an increased yield should be expected for the intermediate enediamide.
Attached Files
MNR13-2 5 hours
MNR13-2 scheme.png
MNR13-2 scheme.png
MNR13-2-INT.png
mnr13-2_frac9-20_1H.pdf
mnr13-2_other fractions_1H.pdf
mnr13-2_others.zip
mnr13-2_frac9-20.zip