All Notebooks | Help | Support | About
5th August 2013 @ 02:16

Repeat of Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through ester synthesis (MD 17-1)

Procedure:

AEW 10-2  (500 mg, 2.14 mmol, 1 equiv.) was dissolved in DMF (8 mL) and oven-dried potassium carbonate (741 mg, 5.4 mmol, 2.5 equiv.) was added. The mixture was stirred at room temperature for 20 minutes, followed by addition of ethyl-2-bromopropionate (0.36 mL, 2.8 mmol, 1.3 equiv.). Reaction mixture stirred for 20 hours (meetings in afternoon, may have been complete before this time).

Work-up: Water added and then reaction mixture partitioned between EtOAc and water. Washed with water, brine and dried over MgSO4. Filtered and evaporated to give a dark orange oil - suspect DMF still present. Dissolved in toluene and applied to a column equilibrated with neat petroleum ether. Washed with ~250 mL of petroleum ether and then rapidly columned with a 2:1 mixture of petrol:EtOAc. Gave a paler yellow/orange oil. NMR confirms product and presence of residual EtOAC. Dried further at the high vac to give a viscous orange oil that slowly crystallised to a yellow semi-solid (680 mg, 2.04 mmol, 95%).

95 mg reserved for charac./testing

Data:

TLC (50% EtOAc in Hexane) ignore splattering from sampler.

AEW 71-1.jpg

1H NMR after column (+ residual EtOAc from column)

AEW 71-1 proton.pdf
AEW 71-1.zip

 

400 MHZ NMR proton, C and F

AEW 71-1.zip
AEW 71-1 proton.pdf
AEW 71-1 nmr13C.pdf

Hazard and Risk Assessment:

See Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through ester synthesis (MD 17-1)

Linked Entries
This entry is linked by:
Attached Files
AEW 71-1 .png
AEW 71-1.jpg
AEW 71-1 proton.pdf
AEW 71-1.zip
AEW 71-1.zip
AEW 71-1 proton.pdf
AEW 71-1 nmr13C.pdf
AEW 71-1.zip