Potassium Iodide → HCID 22391384, compound

HRID 2113109Notes

Reaction equation

HRID 2113109 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:26](Br)[C:27]#[CH:28]>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:27]#[CH:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 22391344HCID 22391344, compound

Product 1

HCID 22391384HCID 22391384, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-3-(4-methoxyphenyl)benzaldehyde (1.14 g, 5 mmol) in DMF (10 mL) was treated with potassium carbonate (2.48 g, 18 mmol), potassium iodide (10 mg) and propargyl bromide (0.67 mL, 6 mmol). The mixture was heated at 80 C for 3 days, then cooled and the solvent removed under reduced pressure. The residue was redissolved in ethyl acetate and washed water then brine. The organic layer was dried over sodium sulphate then the solvent removed under reduced pressure and the residue purified by column chromatography (3/1 hexane/ethyl acetate) to afford 0.078 g of title compound.

Workup

  1. temperatureThe mixture was heated at 80 C for 3 days
  2. temperaturecooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was redissolved in ethyl acetate
  5. washwashed water
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customthe residue purified by column chromatography (3/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-73e6949718fa4421b9e382a4d0ae1f81
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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