Acetone → HCID 63656854, compound

HRID 1189273Notes

Reaction equation

HRID 1189273 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. customThe solvent was 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-ebf6a724e02b4a61af3695b2a2440e2c
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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