Ethyl Acetate → 2-Azido-1-phenylethanone
Reaction equation
C(O[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][C:11]=1C(F)(F)F)CCCCCCC.CCOC(C)=O.[N-:29]=[N+:30]=[N-:31].[Na+]>C(Cl)Cl.CO>[N:29]([CH2:17][C:16]([C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)=[O:18])=[N+:30]=[N-:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customThe solvent was removed in vacuo
- dissolutionre-dissolved in DMF (10 mL)
- stirringthe resulting mixture was then stirred at room temperature for 2 hrs
- customThe solvent was removed in vacuo
- customthe product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c9f9d90d64df4a12a809f43cb844cef2
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759370B2
Reaction notes
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