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10th August 2012 @ 07:12
Mnr: 41-50
Repeat of MNR41-16 but starting with KAB19-1

MNR44-1%20scheme.png
mnr44-1%20table.PNG

To a solution of KAB19-1 (0.1 g, 0.37 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.048 mL, 0.67 mmol), 2,6-lutidine (0.06 mL, 0.52 mmol, fresh out of a new bottle). The reaction was then stirred at room temperature (19 °C) for 2.5 hours.

After 2.5 hours a sample was taken for mini workup and LCMS. The reaction was left to shake.

TLC after 2.5 hours showed signs of some reaction but not completion. Reaction left over the weekend due to time constraints.

mnr44-1_TLC_2hour.jpg


LCMS

After 2 hours the LCMS showed what looked like significant product with a retention time of 28 minutes.

mnr44-1_2hours.pdf


Work Up

-Monday morning

The mixture was washed with EtOAc (20 mL)saturated sodium bicarbonate solution (25 mL). The aqueous layer was extracted with ethyl acetate (3 × 30 mL). The organic fractions were combined, dried over MgSO4, filtered and concentrated under reduced pressure to yield a yellow solid (0.157 g)
Attached Files
mnr44-1 table.PNG
MNR44-1 scheme.png
mnr44-1_TLC_2hour.jpg
mnr44-1_2hours.pdf