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

HRID 419404노트

반응식

HRID 419404 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-e53652c4febb4e6abf906f2dc9737978
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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