Hydrochloric Acid → Ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetate

Participants

Reaction Steps

To a stirred solution of 3-isopentyl-2-phenylthiazolidin-4-one (0.25 g, 1 mmol) in THF was added LDA (1.1 ml of ˜1 M in THF; freshly prepared from nBuLi and Diisopropylamine) at −78° C. and the reaction mixture was allowed to warm to room temperature. Ethyl glyoxalate (0.24 ml of ˜50% w/v in toluene, 1.2 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 1 N HCl and extracted with EtOAc (3×). The organics were combined, washed with brine, dried (MgSO4) and evaporated to dryness. Purification by column chromatography (5 to 15% EtOAc in Hx) gave the desired product as an oil.

Provenance & Evidence