Triethylamine → HCID 86672575, compound

Temperature

-10 °C

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].

1. customforming a white solid
2. customThe solvent was removed by rotatory evaporation
3. dissolutionthe residue was dissolved in CH2Cl2 (20 mL)
4. washthe organic layer was consecutively washed with a mixture of water (200 mL) and HCl (10% aqueous solution, 10 mL)
5. additiona mixture of water (200 mL) and NaOH (10% aqueous solution, 10 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. filtrationfiltered
8. customAfter removal of the solvent
9. customthe residue was purified by column chromatography on silica gel (10% EtOAc/Hexanes)

ORD record

ord-f4479fa7b77d432bb26bd0c93d76bb26

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946296B2