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

HRID 1687541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1687541
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b630c66bef414165b5417fb68b344c6f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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