Hydrochloric Acid → HCID 67099687, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-Chlorophenyl)-tetrahydrofuran-3-carboxylic acid (375.2 mg, 1655 μmol) was mixed with thionyl chloride (1.21 mL, 16554 μmol) and heated at 70° C. for 3 hours. The solution was cooled, concentrated in vacuo, and pumped on under high vacuum for 3 hours. To a flame-dried round bottom flask containing diethyl malonate (0.25 mL, 1655 μmol) in ACN (3 mL), was added MgCl2 (158 mg, 1655 μmol). The resulting solution was cooled to 0° C. The reaction was then stirred for 15 minutes at 0° C. To the resulting mixture was slowly added TEA (0.48 mL, 3476 μmol), and the reaction was stirred at room temperature for 3 hours. The acid chloride intermediate in ACN (1.9 mL), was added to the malonate solution, and the resulting mixture was stirred at 50° C. for 13 hours. The reaction was then cooled and concentrated in vacuo to give a light yellow solid which was mixed with 1N HCl and EtOAc. The aqueous layer was extracted with EtOAc (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica flash chromatography (10-30% EtOAc/hexane) gave the title compound as a light yellow oil. MS m/e=369.2 (M+H)+.

Provenance & Evidence