Potassium Carbonate → 1-(tert-Butyl)-3-ethynylbenzene

HRID 2377425Notes

Reaction equation

HRID 2377425 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[CH:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 14989665(3-tert-Butyl-phenylethynyl)-trimethyl-silane2×

Product 1

HCID 149896671-(tert-Butyl)-3-ethynylbenzeneYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution 3-tert-butyl-trimethylsilanylethynyl benzene (Intermediate 102, 0.47 g, 2.04 mmol) in methanol (20 mL) was treated with potassium carbonate (2.8 g, 20.2 mmol) and the resulting reaction mixture was stirred at ambient temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as a light yellow oil (0.125 g, 39%).

Workup

  1. customthe resulting reaction mixture
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-348071eba505441d808711fadeafbc1a
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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