Potassium Carbonate → HCID 14650385, compound

HRID 2073901Notes

Reaction equation

HRID 2073901 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]([OH:19])=[CH:15][CH:14]=1.[Cl:20][CH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[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:14]=[CH:15][C:16]([O:19][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[CH2:21][Cl:20])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119191,2-Bis(chloromethyl)benzeneHCID 109887374-[(Quinolin-2-yl)methoxy]phenol

Product 1

HCID 14650385HCID 14650385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (10.11 mmol) of 4-((quinolin-2-yl)methyloxy)phenol, (30.33 mmol, 3 equiv.) of 2-chloromethylbenzyl chloride and 4.2 g (30.33 mmol, 3 equiv) of K2CO3 in 100 mL of 8:1--acetone:DMF is refluxed for 24 hrs. The mixture is poured into ice-water and allowed to stand for 11/2 hours. The precipitate that forms is filtered off, redissolved in EtOAc, dried, and concentrated in vacuo. The crude product is filtered by flash column chromatography to afford 2-(4-((quinolin-2-yl)methyloxy)phenoxymethyl)benzyl chloride which is used directly in the next step.

Workup

  1. custom2 hours
  2. filtrationThe precipitate that forms is filtered off
  3. dissolutionredissolved in EtOAc
  4. customdried
  5. concentrationconcentrated in vacuo
  6. filtrationThe crude product is filtered by flash column chromatography

Sources & evidence

ORD record
ord-62f1c11c893d46449b98cec53ca8ba54
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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