Cesium fluoride → HCID 18679597, compound

HRID 1934497Notes

Reaction equation

HRID 1934497 reaction equation
C[Si](C)(C)[O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[CH2:5].[F-].[Cs+].[F:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[OH:35])=[O:28])[CH:21]=[CH:22][C:23]=1[F:24]>CS(C)=O>[F:17][C:18]1[CH:19]=[C:20]([CH:25]([CH2:3][C:4]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2)=[O:5])[CH2:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[OH:35])=[O:28])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 100824371-Trimethylsilyloxy-1-(4-chlorophenyl)ethyleneHCID 54335129HCID 54335129, compound

Product 1

HCID 18679597HCID 18679597, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

1-Trimethylsilyloxy-1-(4-chlorophenyl)ethylene (7.0 mmol; prepared according to J. Chem. Soc.,Perkin Trans. I 1989, 1585) and CsF (0.27 g, 1.76 mmol) were added to a suspension of 3-(3,4-difluorophenyl)-1-(2-hydroxyphenyl)-2-propen-1-one on Wang resin (2.0 g, 1.76 mmol) in dimethyl sulfoxide (30 mL). The reaction mixture was heated to 70° C. for 3 h and the reaction was quenched with 10% AcOH/CH2Cl2. The resin was filtered, washed with DMF (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight to give 3-(3,4-difluorophenyl)-1-(2-hydroxyphenyl)-5-(4-chlorophenyl)-1,5-pentanedione on Wang resin.

Workup

  1. customthe reaction was quenched with 10% AcOH/CH2Cl2
  2. filtrationThe resin was filtered
  3. washwashed with DMF (×2)
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-64a495022d394006ac217a7bf6d06237
Source dataset
uspto-grants-2002_05
Patent number
US06384057B1

Reaction notes

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