Potassium Carbonate → 6-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one

HRID 1296696ノート

反応式

HRID 1296696 の反応式
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([OH:18])=[C:6]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:19][CH3:20])[O:18][C:30](=[O:31])[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:33])[F:34])=[CH:28][CH:27]=1)=[C:8]2[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 589131241-(5-Bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone

生成物 1

HCID 589131126-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one収率 85.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(5-bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone (0.64 g, 1.9 mmol), 4-trifluoromethylphenylacetic acid (0.78 g, 3.8 mmol), carbonyl diimidazole (0.62 g, 3.8 mmol), N,N-dimethylaminopyridine (0.12 g, 1.0 mmol), and potassium carbonate (0.52 g, 3.8 mmol) in DMF (15 mL) was heated within an 80° C. oil bath overnight. The cooled reaction mixture was poured into water and extracted with EtOAc. Organic extracts were combined and washed with water and saturated sodium chloride in succession, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material purified using silica gel flash column chromatography (1:2 EtOAc:hexanes) to provide the title compound (0.82 g, 85%). MS (ESI) m/z 505.0 (M+1)+, 507.0 (M+1+2)+.

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. washwashed with water and saturated sodium chloride in succession
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material purified

出典と根拠

ORDレコード
ord-f74eb17b4620424ab11034f3612f1096
出典データセット
uspto-grants-2007_07
特許番号
US07247646B2

反応ノート

読み込み中…