Cesium fluoride → HCID 18679589, compound

HRID 1633512Notes

Reaction equation

HRID 1633512 reaction equation
C[Si](C)(C)[O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)=[CH2:5].[F-].[Cs+].[F:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[OH:38])=[O:31])[CH:24]=[CH:25][C:26]=1[F:27]>CS(C)=O>[F:20][C:21]1[CH:22]=[C:23]([CH:28]([CH2:3][C:4]([C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)=[O:5])[CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[OH:38])=[O:31])[CH:24]=[CH:25][C:26]=1[F:27]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 13451205Trimethyl{[1-(naphthalen-2-yl)ethenyl]oxy}silaneHCID 54335129HCID 54335129, compound

Product 1

HCID 18679589HCID 18679589, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

1-Trimethylsilyloxy-1-(naphthalen-2-yl)ethylene (7.0 mmol; prepared according to J. Chem. Soc.,Perkin Trans. I 1989, 1585) and CsF (0.27 g, 1.76 nmol) 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-(naphthalen-2-yl)-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-ccb8622b67264453ab96261b4ca336d2
Source dataset
uspto-grants-2003_01
Patent number
US06503917B1

Reaction notes

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