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21st November 2012 @ 22:00
AEW%2023-1.png

N.B. Heating in sealed vials, take heed of HIRAC and cautions outlined in reaction procedure

AEW 5-2 (87 mg, 0.3 mmol, 1 equiv.) and InBr3 (52 mg, 0.15 mmol, 0.5 equiv) were weighed into a mL screw cap vial containing a magnetic stirrer. The vials were flushed with Ar and sealed. Freshly distilled CHCl3 (1.5 mL) and then Et3SiH (0.95 mL, 6 mmol, 20 equiv.) were added under an atmosphere of Ar. The sealed vials were placed in an pre-heated aluminium heating block and left to stir at 60 ˚C. Blast shield was installed at the front of the heater stirrer plate. Reaction mixture turned from colourless suspension to orange solution on heating. After 6 hours, the reaction was stopped and allowed to cool. Water (10 mL) was added and the reaction mixture stirred at room temperature for 30 minutes until the orange colour had disappeared. Extracted into DCM, dried over MgSO4, filtered and evaporated to yield an orange solid (50 mg). 1H NMR shows trace of product and LCMS shows correct mass for product. Will attempt purification by HPLC.

LCMS and Crude NMR:
AEW 23-3 6 hours.zip
AEW 23-3 6HOURS.pdf
AEW23-3 LCMS Trace.pdf


Reaction mixture after 6 hours:
AEW 23-3 reaction mixture.jpg


Reaction mixture after stirring with water for 30 minutes:
AEW 23-2 after 30 mins stirring with water.jpg


Hazard and Risk Assessment:
HIRAC AEW 23-1.pdf

Safe set-up:
Apparatus.jpg


Reference:
DOI: 10.1021/jo070814z

See Also:
Reduction of 2-amino-2-oxoethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (AEW 23-1) and Reduction of 2-amino-2-oxoethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (AEW 23-2)
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Attached Files
AEW 23-3 reaction mixture.jpg
AEW 23-2 after 30 mins stirring with water.jpg
AEW23-3 LCMS Trace.pdf
AEW 23-3 6HOURS.pdf
AEW 23-3 6 hours.zip