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

HRID 1687541ノート

反応式

HRID 1687541 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b630c66bef414165b5417fb68b344c6f
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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