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10th August 2012 @ 07:17
Mnr: 41-50
Repeat of MNR41-16 but starting with KAB22-1


To a solution of KAB22-1 (0.1 g, 0.39 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.05 mL, 0.71 mmol), 2,6-lutidine (0.064 mL, 0.55 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.



After 2 hours the LCMS showed what could be traces of product but the MS was very messy in that region and could therefore have resulted in product forming in the MS?


The reaction was left to sit for a couple of days due to other commitments but was eventually worked up to see if any product was present.

The mixture was washed saturated sodium bicarbonate solution (15 mL) and 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 oil that slowly crystallised (0.118 g)

Crude NMR showed degradation products but not starting material, there are possible signes of product but a column is required first


TLC's ran in 20%, 40% and 60% EtOAc/Hexane

Column:- 25-100% EtOAc

The only spot to come off the column was the top stop over fractions 1-7 while the solvent was still at 20% EtOAc, even flushing the column did not result in collecting the other spots.
Attached Files
mnr46-1 table.PNG
MNR46-1 scheme.png