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

HRID 66926

反応式

HRID 66926 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6395Methanesulfonic Acid触媒HCID 664601,1,3,3-Tetramethylguanidine触媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-aa0214dade6640c69e0700ce2b97d467
出典データセット
uspto-grants-1982_08
特許番号
US04343939

関連ノート

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