Citric Acid → 1,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanol

HRID 1378399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378399
[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:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](=[O:42])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:26][CH:25]=2)=[CH:15][CH:14]=1.C(O)C.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[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:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]([OH:42])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:26][CH:25]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 107928071,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone

Produkt 1

HCID 105069561,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanolAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1,5-bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone (2.21 g, 4 mmol), prepared as in step 3, in dioxane (15 mL) and ethanol (35 mL) was added NaBH4 (152 mg, 4 mmol) and the resulting mixture was refluxed for 30 minutes. The solution was then cooled to room temperature, acidified to pH 5 with 10% citric acid and concentrated in vacuo. To the residue was added water (50 mL) and the precipitated solid was filtered to afford 1,5-bis(4-(2-quinolylmethoxy)phenyl)-3-pentanol (2.3 g).

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. concentrationconcentrated in vacuo
  3. additionTo the residue was added water (50 mL)
  4. filtrationthe precipitated solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-e00ee011f41042b1923bb2b9aa02b9c0
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668146

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