Water → Ethyl 2-(6-quinolinyloxy)-2-(ethoxy)acetate

HRID 1244806Notes

Reaction equation

HRID 1244806 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.Cl[CH:19]([O:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>C(O)(C)(C)C.[I-].[K+]>[N:14]1[C:15]2[C:10](=[CH:9][C:8]([O:7][CH:19]([O:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 113746-HydroxyquinolineHCID 2724873Ethyl 2-chloro-2-ethoxyacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21923123Ethyl 2-(6-quinolinyloxy)-2-(ethoxy)acetateYield 64.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6386tert-ButanolSolvent

Procedure

Potassium t-butoxide (3.15 g) was dissolved in t-butyl alcohol (20 ml) and stirred for 10 minutes at ambient temperature. 6-Hydroxyquinoline (3.0 g) was added, the resulting dark green solution was stirred for 15 minutes, and then ethyl 2-chloro-2-ethoxyacetate (4.22 g, 90% pure) added, followed by a catalytic amount of potassium iodide (0.005 g). The mixture was stirred for 18 hours, poured into water and extracted with chloroform. The organic fraction was washed with brine, water, and dried over magnesium sulphate. The solvent was evaporated to give a brown oil, which was purified by flash chromatography on silica gel, eluting with a gradient of ethyl acetate:hexane (1:2 to 4:1) to give ethyl 2-(6-quinolinyloxy)-2-(ethoxy)acetate as a pale brown oil (3.68 g).

Workup

  1. stirringthe resulting dark green solution was stirred for 15 minutes
  2. stirringThe mixture was stirred for 18 hours
  3. extractionextracted with chloroform
  4. washThe organic fraction was washed with brine, water
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated
  7. customto give a brown oil, which
  8. customwas purified by flash chromatography on silica gel
  9. washeluting with a gradient of ethyl acetate:hexane (1:2 to 4:1)

Sources & evidence

ORD record
ord-a0565f49269a425281f6f6cc06816d80
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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