Trifluoroacetic acid → (2-Chloro-phenyl)-(3-hydroxy-pyridin-2-yl)-methanone
Reaktionsgleichung
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[C:22]([O:23]COCC[Si](C)(C)C)=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:16]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:16]Komponenten
4
Versuchsvorschrift
Add trifluoroacetic acid (5 mL) to a solution of (2-chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanone (195 mg, 0.54 mmol) in CH2Cl2 (3 mL), stir for 30 minutes. Concentrate; dissolve in 20% i-PrOH/CHCl3, wash with saturated NaHCO3 solution (×2). Dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-30% Et2O/hexanes to afford the title compound (102 mg, 82%) as white solid. MS(IS) 233.9 (M+1). TLC: Rf=0.20 (25% Et2O/hexanes).