Cesium fluoride → HCID 18679600, compound

HRID 1633517Notes

Reaction equation

HRID 1633517 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+].[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](=[O:39])[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][C:33]2[O:36][CH2:37][O:38][C:32]=2[CH:31]=1>CS(C)=O>[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](=[O:39])[CH2:28][CH:29]([C:30]1[CH:35]=[CH:34][C:33]2[O:36][CH2:37][O:38][C:32]=2[CH:31]=1)[CH2:3][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)=[O:5]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 2617033-(1,3-Benzodioxol-5-yl)-1-(2-hydroxyphenyl)-2-propen-1-oneHCID 13451205Trimethyl{[1-(naphthalen-2-yl)ethenyl]oxy}silane

Product 1

HCID 18679600HCID 18679600, 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 mmol) were added to a suspension 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)-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 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)-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-6ba79981e3ee4925b9c9d64cea306934
Source dataset
uspto-grants-2003_01
Patent number
US06503917B1

Reaction notes

Loading…