Trifluoroacetic anhydride → 2-Methoxy-3-nitro-5,6,8,9-tetrahydrobenzocyclohepten-7-one

HRID 1687541Notes

Reaction equation

HRID 1687541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:28]([O-])([O-:30])=[O:29].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[C:4]([N+:28]([O-:30])=[O:29])=[CH:5][C:6]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 24434Potassium NitrateHCID 575225112-methoxy-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one

Product 1

HCID 575225132-Methoxy-3-nitro-5,6,8,9-tetrahydrobenzocyclohepten-7-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Methoxy-5,6,8,9-tetrahydro-benzocyclohepten-7-one (6.00 g, 0.0315 mol) was dissolved in Acetonitrile (280 mL, 5.4 mol) and was added to a mixture of Trifluoroacetic anhydride (13.4 mL, 0.0946 mol) in Acetonitrile at 0° C. Potassium nitrate (3.19 g, 0.0315 mol) was then added and the reaction was allowed to warm to room temperature. When HPLC showed consumption of starting material, the mixture was poured over saturated sodium bicarbonate, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). The gradient run was 0% EA-50% EA. Combined fractions were reduced en vacuo to afford 3.62 (49%) of 2-Methoxy-3-nitro-5,6,8,9-tetrahydro-benzocyclohepten-7-one and 1.80 grams (25%).

Workup

  1. customconsumption of starting material
  2. additionthe mixture was poured over saturated sodium bicarbonate
  3. extractionorganics were extracted with ethyl acetate/dichloromethane
  4. dry with materialCombined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-b630c66bef414165b5417fb68b344c6f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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