Potassium Iodide → HCID 22391384, compound

HRID 460131Notes

Reaction equation

HRID 460131 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-6e6e4bd4b6614ddc953130061ad1679d
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

Loading…