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

HRID 1378399Notes

Reaction equation

HRID 1378399 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 105069561,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanolYield 103.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e00ee011f41042b1923bb2b9aa02b9c0
Source dataset
uspto-grants-1997_09
Patent number
US05668146

Reaction notes

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