Ethyl Acetate → 2-Azido-1-phenylethanone

Participants

Reaction Steps

To a solution of 1-(4-(Octyloxy)-3-(trifluoromethyl)phenyl)ethanone (D1) (0.5 g, 1.0 equivalent) in CH2Cl2/MeOH (4:1, 10 mL) was added Bu4NBr3 (0.76 g, 1.0 equiv). The reaction mixture was stirred at room temperature for 3 hours. TLC (4:1, Hex/EtOAc), Rf=0.6. The solvent was removed in vacuo, and re-dissolved in DMF (10 mL). NaN3 (0.31 g, 3.0 equiv) was added to the reaction and the resulting mixture was then stirred at room temperature for 2 hrs. The solvent was removed in vacuo and the product was purified by silica gel column chromatography using the Combi-Flash system (Hex:EtOAc) to give the azido-acetophenone product. TLC (4:1, Hex/EtOAc), Rf=0.4. The residue was then dissolved in concentrated HCl (1.0 mL) and MeOH (20 mL). 10% Pd/C (100 mg) was added and the mixture stirred under an atmosphere of H2 (g) for 3 hours. The reaction mixture was then filtered and evaporated to dryness to give the title product as a yellow solid 98% (570 mg yield). TLC (4:1, Hex/EtOAc), Rf=0.6.

Provenance & Evidence