Potassium Carbonate → HCID 22671209, compound

HRID 1006865Notes

Reaction equation

HRID 1006865 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[C:14]2[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:17][N+:26]=1[O-:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

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

Product 1

HCID 22671209HCID 22671209, 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-d89092ae752b4524b502804fbacc4f26
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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