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

HRID 1016368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1016368
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e8952e8490ef4710b5c38a616ddb8d2a
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476018B1

Notizen zur Reaktion

Wird geladen…