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

HRID 1792972

반응식

HRID 1792972 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-080b4e4ea4564d1bb6cac95e8adafada
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078431B2

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