Potassium Carbonate → Ethyl 2-(2-(3-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionate

HRID 2073899Notes

Reaction equation

HRID 2073899 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.Br[CH2:21][C:22]1[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=1[O:24][CH:25]([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:21][C:22]1[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=1[O:24][CH:25]([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 11808300Ethyl 2-(2-bromomethylphenoxy)propionate

Product 1

HCID 11113252Ethyl 2-(2-(3-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5.23 mmol) of 3-(quinolin-2-yl)methyloxyphenol and (5.23 mmol) of the bromide from step B in 90 ml of 8:1--acetone:DMF is added 1.52 g (10.97 mmol, 2.1 equiv) of K2CO3. The mixture is refluxed overnight, then partitioned between EtOAc and H2O. The organics are dried, filtered, and concentrated in vacuo. This is then purified by flash column chromatography to give ethyl 2-(2-(3-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionate which is used directly in the next step.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. custompartitioned between EtOAc and H2O
  3. customThe organics are dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis is then purified by flash column chromatography

Sources & evidence

ORD record
ord-ae4cb130ac5740f383aa6d9a5efaa0b5
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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