Methyl iodide → HCID 15078759, compound

Participants

Reaction Steps

Z-3-(4'-Methoxybenzylthio)-3-phenyl-2-propenoic acid (5.46 g, 18.2 mmol) was suspended in 22 mL of dry acetonitrile. Addition of DBU (3.30 mL, 22.1 mmol) gave a clear yellow solution. The mixture was stirred in an ice bath and iodomethane (1.32, 21.2 mmol) was then added over 5 minutes. After an additional 15 minutes, the ice bath was removed and the solution was stirred for 1.25 hours. The reaction was poured into 100 mL of ethyl acetate and washed with 75 mL of water, 2×25 mL of 2N aqueous hydrochloric acid, 2×25 mL of saturated aqueous sodium bicarbonate, and 25 mL of saturated aqueous sodium chloride. The ethyl acetate solution was dried over sodium sulfate, decanted, and evaporated to give 4.53 g of crude methyl Z-3 (4'-methoxybenzylthio)-3-phenyl-2-propenoate as pale yellow crystals.

Provenance & Evidence