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

Participants

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)-furan-2-yl]-thioacetamide (3.20 g, 14.06 mmol) and ethylbromopyruvate (2.07 mL, 14.06 mmol) in ethanol (40 mL) was stirred for 30 min 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=0.86 min, [M+H]+=280.30.

Provenance & Evidence