Potassium Carbonate → HCID 22503278, compound

HRID 1251094Notes

Reaction equation

HRID 1251094 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:22]=[CH:21][C:20](OC)=[CH:19][C:16]=1[CH:17]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N+:26]([O-:27])=[CH:17][C:16]2[C:15]([CH:14]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22503528HCID 22503528, compound

Product 1

HCID 22503278HCID 22503278, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[2-(4-Benzyloxybutyl)ethynyl]-5-methoxybenzaldehyde (2.60 g), hydroxylamine hydrochloride (0.63 g) and sodium acetate (0.78 g) were reacted in ethanol (30 ml) at 60° C. for 2 hr. Potassium carbonate (2.0 g) and water (5 ml) were added to the resulting reaction mixture, which was then heated under reflux for 12 hr. The reaction solution was evaporated, and the resulting residue was extracted with methylene chloride, washed with brine, and then dried. The solvent was removed and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 2.0 g of the title compound as a brown amorphous.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 12 hr
  3. customThe reaction solution was evaporated
  4. extractionthe resulting residue was extracted with methylene chloride
  5. washwashed with brine
  6. customdried
  7. customThe solvent was removed
  8. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-384cf674c5b74ec88de135516c66ea53
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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