Potassium Carbonate → HCID 54097931, compound

HRID 1779961Notes

Reaction equation

HRID 1779961 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)#[N:18].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]3)=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 14131535HCID 14131535, compound

Product 1

HCID 54097931HCID 54097931, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 50 ml of 2-butanone, 1.2 g of methyl 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-acetate and 1.60 g of 4-cyanobenzyl bromide were dissolved, 1.51 g of potassium carbonate was added, and the mixture was refluxed by heating for 12 hours. Most of the solvent was distilled off under reduced pressure. The concentrated residue was mixed with water and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The concentrated residue was purified by silica gel column chromatography using a mixture, ethyl acetate:n-hexane=1:3, as a developer to yield 1.7 g of the entitled compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 12 hours
  3. distillationMost of the solvent was distilled off under reduced pressure
  4. additionThe concentrated residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe concentrated residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-875153e5810b493787cd346939c5e31b
Source dataset
uspto-grants-1997_05
Patent number
US05629321

Reaction notes

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