Cesium carbonate → HCID 19864853, compound

HRID 1200256Notes

Reaction equation

HRID 1200256 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.[I-].[K+]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[O:12][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 132801193-(1,3-Dioxolan-2-yl)phenol

Product 1

HCID 19864853HCID 19864853, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A solution of the ketal of Step A, above, (10 g, 0.06 mol), 2-chloromethylquinoline (10.6 g, 0.06 mol), cesium carbonate (20.0 g, 0.06 mol) and potassium iodide (0.16 g, 0.001 mol) in 250 ml acetone is refluxed 20 hours. The solution is filtered through Celite and silica gel and the solvent is removed in vacuo. The resulting crude solid is recrystallized using 2-propanol to give 13.7 g of crystalline solid (74% yield) m.p. 67°-69° C.

Workup

  1. filtrationThe solution is filtered through Celite and silica gel
  2. customthe solvent is removed in vacuo
  3. customThe resulting crude solid is recrystallized

Sources & evidence

ORD record
ord-3dcfdd0f16e14ffb833bea4784816fe0
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

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