Sodium ethoxide → HCID 67099826, compound

Participants

Reaction Steps

A mixture of (Z)-ethyl 4-(3-chloro-2-(3-ethoxy-1-hydroxy-3-oxoprop-1-enyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (0.14 g, 0.37 mmol) in 5 mL EtOH was treated with NaOEt (from 0.1 g Na reacted with 5 mL EtOH). The mixture was stirred at room temperature for 2 hours, quenched with 20 mL water, and neutralized with 5N HCl to pH=5. The mixture was extracted with EtOAc 3×50 mL. The combined organic layers were washed with saturated NaCl (20 mL), dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by column chromatography (10-40% EtOAc/hexane) to give 67 mg white solid. MS m/e: (M+H)+ 337.

Provenance & Evidence