Dimethyl Sulfoxide → HCID 18679596, compound

HRID 1934505Notes

Reaction equation

HRID 1934505 reaction equation
C[Si](C)(C)[O:3][C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[CH2:5].[F-].[Cs+].[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:34])[CH:23]=[CH:24][CH2:25][C:26]1S[CH:29]=[C:28]2[O:31][CH2:32][O:33][C:27]=12.[CH3:35]S(C)=O>>[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:34])[CH2:23][CH:24]([C:25]1[CH:35]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[CH2:3][C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[O:5]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25953Cesium fluorideHCID 13484121HCID 13484121, compoundHCID 70171603HCID 70171603, compound

Product 1

HCID 18679596HCID 18679596, compound

Conditions

Temperature
70 °C

Procedure

1-Trimethylsilyloxy-1-(thiophen-3-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-methylenedioxythenyl)-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-(thiophen-3-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-68205baa32a1468bad2c37d9b3432e86
Source dataset
uspto-grants-2002_05
Patent number
US06384057B1

Reaction notes

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