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25th October 2011 @ 00:40
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Conversion of PMY 15-2 to its mesylate and then displacement by PMY 9-1 to form the ether analogue of TCMDC-123794.

Reaction Scheme

Reaction start time: 12.00 25/10/11
PMY 15-2 (50 mg, 0.23 mmol, 1 equiv.) and triethylamine (0.03 mL, approx 0.23 mmol, 1 equiv.) were stirred in DCM (2 mL) at 0 °C. Methanesulfonyl chloride (18 μL, 0.23 mmol, 1 equiv.) was added. After 30 minutes, TLC does not shows SM to be impure (NMR confirms, see: Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-2)). PMY 9-1 (60 mg, 0.23 mmol, 1 equiv.) in DCM (1 mL) and triethylamine (0.03 mL, approx 0.23 mmol, 1 equiv.) was added. Reaction abandoned due to poor SM.

TLC (40% EtOAc/hexane) visualised with UV and vanillin:
TLC 30 minutes


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Reaction Scheme
Risk Assessment
TLC 30 minutes