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15th November 2011 @ 22:15
Preparation of starting material for the Ugi reaction as for MNR4-1
MNR21-1%20scheme.png
mnr21-1%20table.PNG

Hazard and Risk Assessment:
HIRAC-MNR21

Procedure
A solution of phenethylamine (25 mL, 75.67 mmol) in ethyl formate (73 mL, 908 mmol) was heated to reflux overnight (15 hours). The remaining ethyl formate and the by-product ethanol were removed under reduced pressure to give yellow liquid.
The crude N-phenethylformamide and triethylamine (31.6 mL, 227 mmol) were dissoved in dry DCM (135 mL) and phosphoryl chloride (7.05 mL, 75.7 mmol) was added dropwise added at 0°C. The mixture was then stirred for 1 h at 0°C and a further 4 h at room temperature.
The mixture was quenched with water and neutralized with NaHCO3 solution. The organic layer was separated and the aqueous solution was extracted DCM (x3). The organic layers were combined, dried over magnesium sulphate, filtered and evaporated afforded a dark brown oil.

** Has data gone missing from this post?

Update, 29/11/11

Column ran 16-17th November - 20-100% EtOAc/Hex

Frac 8-10 1.873 g, orange oil which slowly crystallized.
Frac 12-15 13.138 g, dark brown oil - mixture of product and what looks like N-phenethylformamide intermediate.

Second colunm ran with co-spots and crude that wasn't loaded onto the first column.

Column 2:- 20-100% EtOAc/Hex

fraction with same rf as major spot above, 0.445 g - similar mixture as above.

This should not have been taken onto the next step! Try a test reaction again with POCl3 to see if we can get conversion this time?

Lab book page complete, MNR
Linked Entries
Attached Files
MNR21-1 scheme.png
mnr21-1 table.PNG
HIRAC MNR21.pdf
mn21-1_2nd col.pdf
mnr21-1_frac 8-10.pdf
mnr21-1_frac 12-15.pdf
mnr21-1.zip