Potassium Iodide → HCID 22391384, compound

HRID 1072234Notes

Reaction equation

HRID 1072234 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-bad52d8ba89f40d8beb59f843755a06a
Source dataset
uspto-grants-2005_06
Patent number
US06908935B2

Reaction notes

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