Iodoethane → 3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

Participants

Reaction Steps

To a slurry of sodium hydride (60% suspension in oil, 7.5 g) and dimethyl formamide (70 ml) was added a solution of the racemic ethyl 2-hydroxy-3-(4-benzyloxyphenyl)propionate of the formula (10) (40 g) obtained according to the procedure described in step (iv) above in dimethylformamide (105 ml) at 5–10° C. over a period of 15–30 minutes. The temperature was allowed to attain room temperature and maintained at the same temperature for 1–3 h Ethyl iodide (36 g) was added slowly by maintaining the temperature at 25–30° C. over a period of 2–3 hours. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was dumped into ice water and extracted with toluene. The combined organic extracts were washed with water and the solvent was removed under reduced pressure to afford the title compound of the formula (12a) (47–48 g, 98–99%).

Provenance & Evidence