Acetone → HCID 63656854, compound

HRID 422460Notes

Reaction equation

HRID 422460 reaction equation
C[SiH](C)C.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].[C:12]([O-])([O-])=O.[K+].[K+].[CH3:18][C:19]([CH3:21])=O>>[CH2:18]([N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=[O:11])[CH2:19][C:21]#[CH:12]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 70435TrimethylsilaneHCID 178516071HCID 178516071, compound

Product 1

HCID 63656854HCID 63656854, compoundYield 5%

Conditions

Temperature
150 °C

Procedure

4-bromobut-1-ynyl)trimethylsilane (700 mg, 3 mmol), pyridin-2-ol (300 mg, 3 mmol) and K2CO3 (900 mg, 6 mmol) were poured into acetone (4.2 ml) and the resulting mixture was heated in the microwave at 150° C. for 7 min The solvent was evaporated and the crude product was dissolved DCM and the organic layer was washed with water. The crude residue was purified over silicagel chromatography (prepacked 5 g silicagel column, DCM/MeOH: 99/1 as eluent) to afford 33 mg of 1-(but-3-ynyl)pyridin-2(1H)-one as a brown oil (Yield: 5%).

Workup

  1. customwas evaporated
  2. dissolutionthe crude product was dissolved DCM
  3. washthe organic layer was washed with water
  4. customThe crude residue was purified over silicagel chromatography (prepacked 5 g silicagel column, DCM/MeOH: 99/1 as eluent)

Sources & evidence

ORD record
ord-32534884cc40488396f3d872ef0d9db3
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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