Potassium Carbonate → Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

HRID 1776311Notes

Reaction equation

HRID 1776311 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1>>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetateYield 106.4%

Conditions

Temperature
90 °C

Procedure

To a stirred solution of ethyl 2-(4-hydroxyphenyl)acetate (20 g, 111.10 mmol) in AcN (200 mL) were added K2CO3 (145.9 g, 333.30 mmol) and 2-(chloromethyl)quinoline (28.50 g, 133.32 mmol) at RT. The reaction mixture was heated at 90° C. for 12 h and then cooled to RT and filtered. The filtrate was concentrated in vacuo. The residue was then diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, a saturated NH4Cl solution, and then dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (38.0 g, 89%) as a solid.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionThe residue was then diluted with water (100 mL)
  5. extractionextracted with EtOAc (3×100 mL)
  6. washThe combined organic layers were washed with water
  7. dry with materiala saturated NH4Cl solution, and then dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75d381c16eba4eb686afd7646697ebe4
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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