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30th October 2012 @ 21:28
Friedels-Craft Acylation of AEW1-1 to give MNR51-2. Repeating the conditions of MNR51-1 but with a longer reaction time. See [url=http://malaria.ourexperiment.org/tcmdc_ap/4223/Repeat_Preparation_of_14Fluorophenyl25dimethyl1Hpyrrole_AEW_11.html]- Synthesis of AEW1-1[/url] [url=http://malaria.ourexperiment.org/tcmdc_ap/5189/FriedelsCraft_Acylation_of_AEW11_to_give_MNR511.html]- Synthesis of MNR51-1[/url] [b]Hazard Assessment[/b] [data]3642[/data] [b]Procedure[/b] reaction on at 7pm 30/10/12 off at 5pm 1/11/12 AlCl3 (2.26 g, 16.9 mmol) was added to a solution of succinic anhydride (0.931 g, 9.30 mmol) and AEW1-1 (1.60 g, 8.46 mmol) in DCM (40 mL). The reaction mixture was stirred at room temperature for 46 hours by which time it had become very thick with possible precipitate. The mixture was concentrated then water (10 mL) was added and the mixture cooled to 0°C and acidified with HCl (37%, 5 mL). The mixture was allowed to warm to room temperature and stirred for 30 min. Again, no solid crashed out, only a red insoluble oil formed. EtOAc (25 ml) was added and the organic laer extracted. The aq layer was then extract with EtOAc (3 x 25 mL), the organics were then combined, dried of magnesium sulphate, filtered and concentrated to give the crude as a red solid. Crude TLC vs MNR51-1 50% EtOAc/Hex [data]3706[/data] Column 40-50% EtOAc/hex frac 7-24 original nmr still had DCM and MeOH - left on hi-vac overnight after overnight on the hivac - 1.156 g [data]3942[/data] Unknown singlet at 3.71 and quartet at 2.67?
Attached Files
mnr51-2_table.PNG
SANY0015.JPG
mnr51-2_frac7-24_1H.pdf