Potassium Carbonate → HCID 22066292, compound

HRID 496309Notes

Reaction equation

HRID 496309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:23])([CH3:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][Si](C)(C)C)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]([CH3:23])([CH3:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22066290[7-(3,5-Dimethoxyphenyl)-7-methyloct-1-yn-1-yl](trimethyl)silane

Product 1

HCID 22066292HCID 22066292, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

[7-(3,5-Dimethoxyphenyl)-7-methyl-1-octynyl]trimethysilane (900 mg, 2.73 mmol) was dissolved in 3.5 mL of anhydrous methanol. Anhydrous potassium carbonate (75 mg, 0.55 mmol, 20 mol %) was added and the heterogeneous mixture was stirred at room temperature, under argon, for 24 h. The reaction mixture was diluted with water and extracted with diethyl ether. The ether extract was dried, concentrated by rotary evaporation and the residue was purified by chromatography on silica gel (5% ethyl ether-petroleum ether) to give 540 mg (76%) of the desilylated product. Anal. calcd. for C17H24O2 C, 78.42; H, 9.29.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. customwas dried
  4. concentrationconcentrated by rotary evaporation
  5. customthe residue was purified by chromatography on silica gel (5% ethyl ether-petroleum ether)

Sources & evidence

ORD record
ord-87494f72400b459eb37933bc8d818b2e
Source dataset
uspto-grants-2005_09
Patent number
US06943266B1

Reaction notes

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