Methyl 3-(2,5-dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)-3-oxopropanoate → 1-(2,5-Dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)ethanone

HRID 1522899ノート

反応式

HRID 1522899 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([O:27][CH3:28])[CH:18]=1)C(OC)=O>CCO.Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH2:12][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[C:19]([O:27][CH3:28])[CH:18]=1

参加物

4

反応物 1

HCID 86682917Methyl 3-(2,5-dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)-3-oxopropanoate

生成物 1

HCID 866829181-(2,5-Dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)ethanone収率 107.1%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
130 °C

実験手順

To a solution of methyl 3-(2,5-dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)-3-oxopropanoate (30.1 g, 73 mmol) in EtOH (400 mL), concentrated HCl (100 mL) was added. The reaction mixture was heated at 130° C. for 3 h, cooled to room temperature, and concentrated. The residue was dissolved in dichloromethane (150 mL) and washed with brine (3×100 mL). The organic layer was dried (Na2SO4), concentrated and purified by silica gel column chromatography (1:10 EtOAc/petroleum ether) to afford the title compound (27.7 g). 1H NMR (DMSO-d6): δ 7.48 (d, 1H), 7.26-7.25 (m, 1H), 7.07-7.03 (m, 1H), 6.93-6.84 (m, 3H), 4.33 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.77 (s, 3H).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane (150 mL)
  4. washwashed with brine (3×100 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (1:10 EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-4b26459ecd784ed682b4c9106deb8609
出典データセット
uspto-grants-2015_07
特許番号
US09078871B2

反応ノート

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