Hydrochloric Acid → HCID 131733003, compound

Participants

Reaction Conditions

Reaction Steps

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl (2E)-3-[4-(benzyloxy)-2-bromophenyl]prop-2-enoate (950 mg, 2.63 mmol, 1.00 equiv), tributyl(1-ethoxyethenyl)stannane (1.434 g, 3.97 mmol, 1.51 equiv), Pd(PPh3)2Cl2 (184.8 mg, 0.26 mmol, 0.1 equiv), N,N-dimethylformamide (15 mL). The resulting solution was stirred overnight at 90° C. in an oil bath. The mixture was cooled to 0° C. before 2N hydrogen chloride (10 mL) was carefully added dropwise. The resulting solution was stirred for an additional 1.0 h at 15° C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:4). The solution was then diluted with 10 mL of H2O. The resulting solution was extracted with 3×15 mL of ethyl acetate and the organic layers combined. The combined extracts were washed with 1×20 mL of water and 1×20 mL of aqueous saturated sodium chloride solution. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 800 mg (89%) of ethyl (2E)-3-[2-acetyl-4-(benzyloxy)phenyl]prop-2-enoate as light yellow oil.

Provenance & Evidence