Potassium Carbonate → Ethyl 2-[4-(cyanomethoxy)phenyl]-2-ethoxycarbonylacetate

HRID 53958Notes

Reaction equation

HRID 53958 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].Br[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:21]([CH2:20][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:17][CH:16]=1)#[N:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 12965552HCID 12965552, compound

Product 1

HCID 21844455Ethyl 2-[4-(cyanomethoxy)phenyl]-2-ethoxycarbonylacetateYield 84.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 150 ml of acetone were added 14.58 g of ethyl 2-ethoxycarbonyl-2-(4-hydroxyphenyl)acetate, 8.8 g of bromoacetonitrile and 9.6 g of anhydrous potassium carbonate. After refluxing under heating for 5 hours, insoluble materials were removed by filtration, and the resulting filtrate was concentrated to dryness. The residue thus obtained was purified by silica gel column chromatography using toluene as an elution solvent, thereby obtaining 14.2 g of ethyl 2-[4-(cyanomethoxy)phenyl]-2-ethoxycarbonylacetate in the form of colorless oil.

Workup

  1. temperatureAfter refluxing
  2. temperatureunder heating for 5 hours
  3. custominsoluble materials were removed by filtration
  4. concentrationthe resulting filtrate was concentrated to dryness
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-92e292c17b7041b783fe9f1f201a5d15
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

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