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20th March 2012 @ 23:51
Yield: 55
Reagent: JRC_2-1
Product obtained in 55% crude yield used in PMY 11-6 and PMY 42-1.

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Synthesis and isolation of the acid chloride of PMY 8-4 for coupling reactions.

Reaction Scheme

Reaction start time: 10.40 21/03/12
Acid JRC 2-1 (500 mg, 2.14 mmol, 1 equiv.) was stirred in dry PhMe (3 mL) and cooled in ice. Thionyl chloride (0.31 mμL, 4.29 mmol, 2 equiv.). The reaction was allowed to warm to room temperature. After 3 hours, the reaction was concentrated under reduced pressure twice from PhMe (3 mL). The residue was triturated twice with hexane (8 + 2 mL) and the filtrate concentrated under reduced pressure to obtain the acid chloride as a yellow solid (298 mg, 55%). The product was used without further purification.

See also:
Synthesis of TCMDC-123812 via acid chloride (PMY 10-6)
Synthesis of pyrrole acid chloride of PMY 8-4 (PMY 32-2)
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (JRC 2-1)
Synthesis of pyrrole acid chloride of PMY 8-3 (PMY 32-1)

Risk and Hazard Assessment:
As for Synthesis of TCMDC-123812 via acid chloride (PMY 10-1).
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