Cesium fluoride → HCID 18679590, compound

HRID 1633522Notes

Reaction equation

HRID 1633522 reaction equation
C[Si](C)(C)[O:3][C:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[CH2:5].[F-].[Cs+].[CH:15]1([CH:21]=[CH:22][C:23]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[OH:32])=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CS(C)=O>[CH:15]1([CH:21]([CH2:3][C:4]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)=[O:5])[CH2:22][C:23]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[OH:32])=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 107025941-Trimethylsilyloxy-1-(furan-2-yl)ethyleneHCID 57223296HCID 57223296, compound

Product 1

HCID 18679590HCID 18679590, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

1-Trimethylsilyloxy-1-(furan-2-yl)ethylene (1.64 g, 9.0 mmol; prepared according to J. Chem. Soc.,Perkin Trans. I 1989, 1585) and CsF (0.41 g, 2.7 mmol) were added to a suspension of 3-cyclohexyl-1-(2-hydroxy-5-fluorophenyl)-2-propen-1-one on Wang resin (3.0 g, 1.8 mmol) in dimethyl sulfoxide (40 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 3.31 g of 3-cyclohexyl-1-(2-hydroxy-5-fluorophenyl)-5-(furan-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-1b823dd06e9c4d1b8b37b3945b669e18
Source dataset
uspto-grants-2003_01
Patent number
US06503917B1

Reaction notes

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