TCMDC_ArylPyrrole

Attempted synthesis of side chain in greater purity. See also

13 μL of conc. HCl was added to a suspension of glycolic acid (1.0 g, 13.2 mmol, 1 equiv.) in 3,4-dihydro-2H-pyran (3.6 mL, 39 mmol, 3 equiv.) and the reaction mixture was heated to 80 ˚C  for 30 minutes.

Volatiles were evaporated, and the resulting residue was purified by flash column chromatography over silica (Ethyl acetate/Petrol 3:7). Two major fractions collected - very streaky TLC plates with elution of all spots. I think that the material deteriorated on storage in the fridge - should have purified immediately. Second fraction cleaner than first - to be used in next reaction AEW 84-1.

http://www.jbc.org/content/276/45/41638.full.pdf+html

Data:

¹H NMR:

Fraction A:

Fraction B:

Hazard and Risk Assessment: