Editing Synthesis of PTDM (section)

=== <br>Synthesis of 2:<br>  ===

[[Image:PTDM_fig_1.jpg]]

(i) <br> 

Dissolve maleic anhydride (100 g, 1.02 mol) in 1 L toluene, add 150 mL (140.7 g, 2.05 mol) furan<br> 

Stir the solution for 3 days according to the literature. <br> 

Filter the product (1), wash with hexanes and dry under vacuum. <br> 

A colorless powder should be obtained. 

<br><br> 

(ii) Follow the same procedure as Lienkamp et.al. with minor modifications. <br> 

Dissolve&nbsp; Compound 1, 10 mol% DMAP and 1.9 equivalents of the 1,3-Di-Boc-2-ethyl guanidine in DCM. <br> 

After all components dissolved, cool down the solution to 0 <sup>o</sup>C in an ice bath, and then add 1 equivalent of EDC.<br> 

Stire the solution over night. <br> 

Dilute the reaction mixture with DCM.<br> 

Wash with 10% KHSO4 (3 x 25 mL) and sat. NaHCO3 solution (3x 25 mL). <br> 

Next, dry the organic phase&nbsp; over Na2SO4 and filtered. <br> 

Reduce the volume of solution by vacuum evaporation.<br> 

Purify the product with a short alumina column. <br> 

Vacuum evaporation of the solvent yields the pure product 2. <br> 

The yield ranged from ~80%.<br>