Potassium Carbonate → 1,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone

HRID 1378398Notes

Reaction equation

HRID 1378398 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1>CN(C=O)C>[N:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:37]=[CH:38][C:29]=1[CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 107071713-Pentanone, 1,5-bis(4-hydroxyphenyl)-

Product 1

HCID 107928071,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanoneYield 113.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,5-bis(4-hydroxyphenyl)-3-pentanone (2.0 g, 8 mmol), prepared as in step 2, and potassium carbonate (2.76 g, 20 mmol) in DMF (40 mL) was treated with chloromethylquinoline (3.55 g, 20 mmol) at room temperature for 36 hours. The mixture was then poured into ice water (200 mL), and the precipitated solid was filtered, washed with water and dried in vacuo to afford crude 1,5-bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone (5 g) which was used without further purification.

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9e9113ccc329412ab5502953c0663ff9
Source dataset
uspto-grants-1997_09
Patent number
US05668146

Reaction notes

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