3-Nitro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine → 4-(3-Nitropyridin-4-yl)cyclohex-3-enone

HRID 2192556Notes

Reaction equation

HRID 2192556 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

HCID 592265423-Nitro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine

Product 1

HCID 592265364-(3-Nitropyridin-4-yl)cyclohex-3-enoneYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

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

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved with ethyl acetate (200 mL)
  3. washwashed
  4. dry with materialThe organic was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58f2e1999ccb4f7783f29ff1661cebe3
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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