Cesium carbonate → 3-(3,4-Difluorophenyl)-1-[2-methoxy-4-(thien-2-yl)phenyl]-2-propen-1-one

HRID 1792972

反応式

HRID 1792972 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][C:4]=1[C:14](=[O:16])[CH3:15].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[F:26])[CH:21]=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[F:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:15][C:14]([C:4]2[CH:5]=[CH:6][C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[CH:8][C:3]=2[O:2][CH3:1])=[O:16])[CH:23]=[CH:24][C:25]=1[F:26]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 5880883,4-DifluorobenzaldehydeHCID 219810692'-Methoxy-4'-(thien-2-yl)acetophenone

生成物 1

HCID 694942253-(3,4-Difluorophenyl)-1-[2-methoxy-4-(thien-2-yl)phenyl]-2-propen-1-one収率 69.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The 2′-methoxy-4′-(thien-2-yl)acetophenone (0.30 g, 1.3 mmol) from Ex-57A and 3,4-difluorobenzaldehyde 0.19 g, 1.3 mmol) were mixed in tetrahydrofuran (THF, 10 mL). Cesium carbonate (1.2 g, 3.9 mmol) was added, and the mixture was stirred at reflux overnight. Upon cooling to room temperature, the mixture was filtered, the filtrate was treated with 0.5 M HCl, and extracted with dichloromethane. The organic phase was dried and evaporated. Silica gel chromatography gave 0.32 g (69%) of the desired 3-(3,4-difluorophenyl)-1-[2-methoxy-4-(thien-2-yl)phenyl]-2-propen-1-one product, m.p. 73-79° C. 1H-NMR (300 MHz, CDCl3): 7.70 (d, 1H), 7.25-7.40 (m, 2H), 6.98-7.15 (m, 7H), 6.49 (d, 1H), 3.89 (s, 3H).

後処理

  1. temperatureat reflux overnight
  2. filtrationthe mixture was filtered
  3. additionthe filtrate was treated with 0.5 M HCl
  4. extractionextracted with dichloromethane
  5. customThe organic phase was dried
  6. customevaporated

出典と根拠

ORDレコード
ord-080b4e4ea4564d1bb6cac95e8adafada
出典データセット
uspto-grants-2006_07
特許番号
US07078431B2

関連ノート

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