3-Nitro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine → 4-(3-Nitropyridin-4-yl)cyclohex-3-enone
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][CH:11]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][CH:11]=1)([O-:3])=[O:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 3-nitro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine (1.0 equiv.) in 20% TFA in CH2Cl2 (0.2 M) was stirred at room temperature overnight. The solvents were removed under reduced pressure. The residue was dissolved with ethyl acetate (200 mL), and washed with sat NaHCO3 (30 mL), and sat NaCl (30 mL). The organic was dried with MgSO4, filtered and concentrated to give 4-(3-nitropyridin-4-yl)cyclohex-3-enone (85%). The crude product was used to next step without further purification. LC/MS (m/z): MH+=218.9, Rt=0.60