Trifluoroacetic acid → 4-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-one

HRID 419404Notes

Reaction equation

HRID 419404 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:19]2[CH2:28][CH2:27][C:22]3(OCC[O:23]3)[CH2:21][CH:20]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:19]2[CH2:28][CH2:27][C:22](=[O:23])[CH2:21][CH:20]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594525898-[3-(Methyloxy)-4-nitrophenyl]-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 594528844-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20% TFA in DCM (25 mL) was added to 8-[3-(methyloxy)-4-nitrophenyl]-1,4-dioxaspiro[4.5]dec-7-ene (900 mg, 3.09 mmol) and the mixture was stirred at rt for approximately 14 h. The reaction was then concentrated under vacuum. The residue was dissolved in EtOAc and aqueous (saturated) NaHCO3. The organic layer was separated, washed with H2O, dried over MgSO4, filtered, then concentrated and purified by silica gel chromatography to give the title compound of step D (520 mg, 2.10 mmol, 68%) as a tan solid. MS (ESI): 248 [M+H]+.

Workup

  1. concentrationThe reaction was then concentrated under vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e53652c4febb4e6abf906f2dc9737978
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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