Ethanol → 2-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-thioacetamide (2.88 g, 11.83 mmol) and ethylbromopyruvate (1.74 mL, 11.83 mmol) in ethanol (34.0 mL) was stirred for 16 h at reflux. The solvent was removed under reduced pressure and the residue was dissolved in EA (150 mL) and washed with 7% aq. NaHCO3 (100 mL). The org. phase was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.24. LC-MS-conditions 02: tR=0.93 min, [M+H]+=296.37.

Provenance & Evidence