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16th November 2012 @ 03:58
Mnr: MNR51-60
Hydrolysis of AEW7-2 to give MNR57-1

See - Synthesis on AEW7-2

MNR57_scheme.png
MNR57-1_table.PNG

Hazard Assessment
HIRAC MNR50.pdf


Procedure

reaction on at 1230pm 16/11/12

NaOH (25.1 g, 628 mmol) was added to a solution of AEW7-2 (62.8 mmol) in EtOH (200 mL) and water (100 mL) and then heated to reflux for 3 hours. The reaction was allowed to cool to room temperature and was then cooled in an ice bath and then acidified to pH 1 using conc. HCl. The brown precipitate was then filtered and rinsed with water to give a crude (wet) off light brown solid. The crude was then recrystallised in Et2O (250 ml) and left to stand overnight. The fine crystals were filtered and washed with Et2O and dried under vacuum (0.802 g). The filtrate was combined with the original washings and concentrated to remove most of the organics and was left in the fridge over night. This was filtered and the dark brown solid was recrystallised in acetone (very messy work up). Again the washing were concentrated as mass recovery was very poor. The above was repeated and a 3rd filter was obtained but as a darker solid as the previous two.

1st filter - 0.802 g, 3.43 mmol, 5%
2nd filter - 4.376 g, 18.7 mmol, 30%
3rd filter - 2.189 g, 9.39 mmol, 15%

Total recovered from filtration - 7.367 g, 31.6 mmol, 50%

The remaining washings were then concentrated and passed through a short column of silica 50-100% EtOAc/Hex

Fracs 1-5 - still to be NMR'd
Fracs 6-17 - still to be NMR'd

NMR
mnr57-1_1st_filter_1H.pdf
mnr57-1_1st_filter_13C.pdf
mnr57-1_1st_filter_19F.pdf
mnr57-1_1st_filter.zip


2nd filter
mnr57-1_2nd_filter_1H.pdf
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Attached Files
MNR57_scheme.png
MNR57-1_table.PNG
mnr57-1_1st_filter_19F.pdf
mnr57-1_1st_filter_13C.pdf
mnr57-1_1st_filter_1H.pdf
mnr57-1_1st_filter.zip
mnr57-1_2nd_filter_1H.pdf
D.png
Comments
Re: Hydrolysis of AEW7-2 to give MNR57-1 by OSDD Malaria
26th January 2014 @ 00:05
OSM-S-4