Cesium carbonate → 5-(Oxiran-2-ylmethoxy)quinoline

HRID 2211223Notes

Reaction equation

HRID 2211223 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.S(C1C=CC(C)=CC=1)(O[CH2:22][CH:23]1[O:25][CH2:24]1)(=O)=O>CN(C)C=O>[O:25]1[CH2:24][CH:23]1[CH2:22][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 160868Glycidyl tosylateHCID 135441757Quinolin-5-ol

Product 1

HCID 112178995-(Oxiran-2-ylmethoxy)quinolineYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

297 g of cesium carbonate was added to 600 ml of dimethylformamide. Further, 83.5 g of 5-hydroxyquinoline was added. The mixture was stirred at 25°-30° C. for 30 minutes. To the reaction mixture was slowly added 109 g of glycidyl tosylate. The resulting mixture was stirred at 25°-30° C. for 15 hours. The reaction mixture was poured into 3 liters of ice water, followed by stirring and extraction with 2 liters of ethyl acetate. The aqueous layer was subjected to extraction with 2 liters of ethyl acetate. The organic layers were combined and washed twice with 2 liters of water. The ethyl acetate layer was dried over anhydrous Glauber's salt and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 76.8 g (yield: 66%) of intended 5-(2,3-epoxypropoxy)quinoline as a light yellow powder.

Workup

  1. stirringThe resulting mixture was stirred at 25°-30° C. for 15 hours
  2. stirringby stirring
  3. extractionextraction with 2 liters of ethyl acetate
  4. extractionThe aqueous layer was subjected to extraction with 2 liters of ethyl acetate
  5. washwashed twice with 2 liters of water
  6. dry with materialThe ethyl acetate layer was dried over anhydrous Glauber's salt
  7. distillationsubjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5343bdf97eab4c42aa5f7964b4ca368d
Source dataset
uspto-grants-1995_10
Patent number
US05463061

Reaction notes

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