Triethylamine → HCID 86672575, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl chloroformate (2.72 mL, 28.52 mmol) was added to a solution of Et3N (4.24 mL, 30.42 mmol) and (trans)-2-[4-(allyloxy)phenyl]cyclopropanecarboxylic acid (Intermediate G, 4.15 g, 19.01 mmol) in dry acetone (50 mL) cooled at −10° C., forming a white solid. After 1 h, a solution of NaN3 (2.23 g, 34.23 mmol) in water (10 mL) was added to the reaction and stirred for additional 30 min. The solvent was removed by rotatory evaporation and the residue was dissolved in CH2Cl2 (20 mL); the organic layer was consecutively washed with a mixture of water (200 mL) and HCl (10% aqueous solution, 10 mL) and a mixture of water (200 mL) and NaOH (10% aqueous solution, 10 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10% EtOAc/Hexanes), affording 4.10 g of (trans)-2-[4-(allyloxy)phenyl]cyclopropanecarbonyl azide [Rf=0.75 (20% EtOAc/Hexanes), white solid, 89% yield].

Provenance & Evidence