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19th January 2012 @ 00:24

Synthesis and isolation of the acid chloride of PMY 8-3 for coupling reactions.

Reaction Scheme

Reaction start time: 11.55 19/01/12
PMY 8-3 (400 mg, 1.71 mmol, 1 equiv.) was stirred in dry PhMe (10 mL). 1 drop DMF added followed by thionyl chloride (0.4 mL, 5.55 mmol, 3.2 equiv.). The reaction was heated to reflux. After 4 hours, reaction cooled and left under nitrogen overnight.Lab electrical shutdown. Reaction concentrated under reduced pressure. Mixture bumped on Büchi, some mass lost. Concentrated twice more from toluene (2 × 25 mL). Brown solid. 1H NMR shows only trace pyrrole peaks. Messy.

1H NMR crude

Risk and Hazard Assessment:
As for Synthesis of TCMDC-123812 via acid chloride (PMY 10-1), except formation of acid chloride at reflux.
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1H NMR crude