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

HRID 324296노트

반응식

HRID 324296 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9cf0c50ce18640fa9cab3275e4abc3c8
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218381B1

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