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

HRID 1687541노트

반응식

HRID 1687541 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b630c66bef414165b5417fb68b344c6f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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