Pyridium p-toluenesulfonate → 4-(5,6-Diphenylpyrazin-2-yloxy)-1-butanol

HRID 1271309Notes

Reaction equation

HRID 1271309 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24]C3CCCCO3)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21909214Pyridium p-toluenesulfonateHCID 229319531-(5,6-Diphenylpyrazin-2-yloxy)-4-(2-tetrahydropyranyloxy)butane

Product 1

HCID 229319914-(5,6-Diphenylpyrazin-2-yloxy)-1-butanolYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.39 g of 1-(5,6-diphenylpyrazin-2-yloxy)-4-(2-tetrahydropyranyloxy)butane was dissolved in methanol and 1.53 g of pyridium p-toluenesulfonate was added, and then the mixture was refluxed for 30 minutes. The reaction solution was cooled, poured into ice water while stirring and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 1.74 g of the desired compound as a colorless crystal having a melting point of 93 to 95° C.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. temperatureThe reaction solution was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d17f7c00f9a74db5a375e45c7d45aae9
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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