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

HRID 419404ノート

反応式

HRID 419404 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e53652c4febb4e6abf906f2dc9737978
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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