Ethylene carbonate → 2-[3-(2-Quinolinyl-methoxy)phenoxy]ethanol

HRID 1016368Notes

Reaction equation

HRID 1016368 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.C(=O)([O-])[O-].[K+].[K+].[O:26]1[CH2:30][CH2:29]OC1=O>O>[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][CH2:29][CH2:30][OH:26]

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 186124902-[3-(2-Quinolinyl-methoxy)phenoxy]ethanolYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(2-Quinolinyl-methoxy)phenol (12.5 g), potassium carbonate (10.4 g) and 1,3-dioxolan-2-one (44 g) were stirred on an oil bath at 100° C. for 2 hours. The mixture was cooled, poured into water and extracted with DCM. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and evaporated. The residue was stirred up in DIPE. The precipitate was filtered off and dried, yielding 11.9 g (80.6%) of 2-[3-(2-quinolinyl-methoxy)phenoxy]ethanol (intermediate 5).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  7. customThe pure fractions were collected
  8. customevaporated
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-e8952e8490ef4710b5c38a616ddb8d2a
Source dataset
uspto-grants-2002_11
Patent number
US06476018B1

Reaction notes

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