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5th September 2011 @ 05:56
Preparation of starting material for the Ugi reaction via the MW37-2 method.

MNR4-1%20scheme.png
MNR4-1%20table.PNG

Hazard and Risk Assessment:
HIRAC MNR4.pdf


A solution of 3,4-dimethoxyphenethylamine (8.4 mL, 50.6 mmol) in ethyl formate (48 mL, 607 mmol, bp 52-54°C) was heated to reflux for 18 h. The remaining ethyl formate and the by-product ethanol were removed under reduced pressure to give yellow liquid.
The crude 2-(3,4-Dimethoxyphenyl)ethylformamide and triethylamine (21.2 mL, 152 mmol) were dissoved in dry DCM (90 mL) and phosphoryl chloride (4.7 mL, 50.6 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.

column (25% EtOAc/hexane), fractions 5-21 - 7.99 g, 83%

1H NMR MNR4-1
1H NMR showed traces of EtOAc, sample put back on the high vac for 2 hours.

Yield, 7.421, 38.8 mmol, 77 % - dark yellow oil


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Attached Files
MNR4-1 scheme.png
HIRAC MNR4.pdf
MNR4-1 table.PNG
1H_mnr4-1.pdf
mnr04-1.zip
mnr4-1.pdf