Ammonium Chloride → HCID 54228975, compound

Participants

Reaction Conditions

Reaction Steps

Sodium metal (2.01 g, 87.43 mmol) cut into small pieces was dissolved in absolute ethanol (67 mL) and the resulting solution cooled to -5° C. A mixture of ethyl azidoacetate (11.32 g, 87.67 mmol) and 3-(4-methoxyphenoxy) benzaldehyde (5.0 g, 21.91 mmol) was added dropwise over 30 min. On completion of addition the mixture was stirred at -5° C. for 4.5 hr, and then kept at room temperature overnight. The red reaction mixture was poured into saturated aqueous NH4Cl solution and extracted (3×) with Et2O. The ethereal extracts were washed (H2O and then saturated aqueous NaCl), dried (MgSO4) and evaporated to give an orange gum which was chromatographed (silica gel; hexane/Et2O; 0-15%). The product: ethyl 2-azido-3-(3-(4-methoxyphenoxy)phenyl)propenoate, was thus obtained as a light yellow gum, 5.5 g (70%).

Provenance & Evidence