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

HRID 1792972Notes

Reaction equation

HRID 1792972 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-080b4e4ea4564d1bb6cac95e8adafada
Source dataset
uspto-grants-2006_07
Patent number
US07078431B2

Reaction notes

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