Water → HCID 13102691, compound

HRID 1757997Notes

Reaction equation

HRID 1757997 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].CS([C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][N:26]=1)(=O)=O.O>C1COCC1>[CH3:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([O:14][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)=[N:26][CH:27]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 132544-PhenoxyphenolHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 13102691HCID 13102691, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.75 g of 4-phenoxyphenol dissolved in a 20 ml THF/20 ml DMSO mixture was added 2.9 g of t-BuOK and then 6.0 g of 2,5-bis(methylsulfonyl)pyridine, and the resulting mixture heated at 58° C. for 11/2 hrs. The reaction mixture was cooled overnight and then poured into 200 ml of water and stirred. A pink-white solid precipitated which was recovered and then dried on a porous plate. Recrystallization and ethanol/CH2Cl2 gave purified 5-(methylsulfonyl)-2-(4-phenoxyphenoxy)pyridine, (88% yield), as slightly pink shiny plates, m.p. 136.5°-138° C.

Workup

  1. temperatureThe reaction mixture was cooled overnight
  2. customA pink-white solid precipitated which
  3. customwas recovered
  4. customdried on a porous plate
  5. customRecrystallization and ethanol/CH2Cl2
  6. customgave

Sources & evidence

ORD record
ord-54121dbef2514f718b28613a008fb96d
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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