p-Toluenesulfonic acid → HCID 69673612, compound

HRID 2283256Notes

Reaction equation

HRID 2283256 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[C:13]2[O:14][CH:15]=[C:16]([C:18](O)(C)[CH3:19])[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:12]=2[C:13]2[O:14][CH:15]=[C:16]([CH:18]=[CH2:19])[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69673406HCID 69673406, compound

Product 1

HCID 69673612HCID 69673612, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(2-(3,5-diphenylpyridazin-4-yl)oxazol-4-yl)propan-2-ol (80 mg, 0.22 mmol) in toluene (4 mL), p-toluenesulfonic acid (20 mg) was added and the reaction mixture was refluxed for 2 h. After completion of starting material, reaction was quenched with solid K2CO3. Solvent was removed under reduced pressure to obtain the crude product that was purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-Hexane) to furnish 2-(3, 5-diphenylpyridazin-4-yl)-4-vinyloxazole (70 mg, 92%) as a gummy liquid.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customAfter completion of starting material, reaction
  3. customwas quenched with solid K2CO3
  4. customSolvent was removed under reduced pressure
  5. customto obtain the crude product that
  6. customwas purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-b3dcbf8e33424ed2b86bdfdb526623b2
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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