Potassium Carbonate → HCID 50998807, compound

HRID 882083Notes

Reaction equation

HRID 882083 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[C:13][Si](C)(C)C)[CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)#[CH:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 673240081315248-52-2

Product 1

HCID 50998807HCID 50998807, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-6-trimethylsilanylethynyl-quinoline (2.1 g, 1.03 mmol, 1 eq) in solution in MeOH (5 mL) was added K2CO3 (5.69 g, 4.12 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 169 mg of 6-ethynyl-2-methyl-quinoline as a yellow crystal (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-57aa7445e11941299bfd5de5c58b7fbc
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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