Potassium Carbonate → HCID 86683820, compound

HRID 882079Notes

Reaction equation

HRID 882079 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:12]#[C:13][Si](C)(C)C)[N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:12]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)#[CH:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67323462HCID 67323462, compound

Product 1

HCID 86683820HCID 86683820, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-trimethylsilanylethynyl-quinoline (140 mg, 0.6 mmol, 1.0 eq) in solution in MeOH (5 mL) was added K2CO3 (324 mg, 2.34 mmol, 4 eq), and the resulting mixture was stirred overnight at room temperature. The solvent was then removed under reduced pressure and water was then added. The aqueous layer was extracted twice with cyclohexane, and then the combined organic layers were washed with brine and dried over MgSO4. After filtration and concentration under reduced pressure the crude product was purified by column chromatography on silica gel (Cyclohexane-EtOAc 99:1) to afford 5-ethynyl-2-methyl-quinoline as a yellow oil (99 mg, 98%).

Workup

  1. customThe solvent was then removed under reduced pressure and water
  2. additionwas then added
  3. extractionThe aqueous layer was extracted twice with cyclohexane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration under reduced pressure the crude product
  7. customwas purified by column chromatography on silica gel (Cyclohexane-EtOAc 99:1)

Sources & evidence

ORD record
ord-1a6c7303d0484432a73e6d672cd402f3
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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