Tetrahydrofuran → Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Ethyl Ester

HRID 66926

반응식

HRID 66926 반응식
[CH3:1][N:2]([C:4]1[CH:20]=[CH:19][C:7]([CH:8]([OH:18])[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].COC.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:25]O.O1CCCC1>CS(O)(=O)=O.CN(C)C(=N)N(C)C.CCCCCC>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([CH:8]([C:7]2[CH:19]=[CH:20][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[O:18][CH2:25][C:24]([O:28][CH2:29][CH3:30])=[O:27])=[CH:10][CH:11]=1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 12184Ethyl GlycolateHCID 927424,4'-Bis(dimethylamino)benzhydrol

생성물 1

HCID 131712796Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Ethyl Ester

시약·촉매·용매 3

HCID 6395Methanesulfonic Acid촉매HCID 664601,1,3,3-Tetramethylguanidine촉매HCID 8058Hexane용매

실험 절차

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), ethyl glycolate 4.04 g, 0.039 mole), 70 ml of tetrahydrofuran, 230 ml of n-hexane and one drop of methanesulfonic acid was refluxed for 2 hours. On completion of the reaction, 2 drops of tetramethylguanidine was added to discharge the blue color. The reaction mixture was filtered hot and the filtrate was cooled. An oily layer formed which was removed and stripped free of solvent; the remaining filtrate was also stripped, leaving an oil. Both samples of oil were combined and chilled. A waxy solid formed which, on repeated trituration with petroleum ether, gave a white solid. Recrystallization from a mixture of petroleum ether/acetone gave a white solid, mp 63°-67.5° C.

후처리

  1. additionwas added
  2. filtrationThe reaction mixture was filtered hot
  3. temperaturethe filtrate was cooled
  4. customAn oily layer formed which
  5. customwas removed
  6. customleaving an oil
  7. temperaturechilled
  8. customA waxy solid formed which
  9. customgave a white solid
  10. customRecrystallization
  11. additionfrom a mixture of petroleum ether/acetone
  12. customgave a white solid, mp 63°-67.5° C.

출처 및 근거

ORD 기록
ord-aa0214dade6640c69e0700ce2b97d467
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343939

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