p-Toluenesulfonic acid monohydrate → HCID 59556702, compound

HRID 1172970Notes

Reaction equation

HRID 1172970 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:22]=3)[C:20]#[N:21])[N:11]=2)=[CH:6][CH:5]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:22]=3)[C:20]#[N:21])[N:11]=2)=[CH:8][CH:9]=1)=[O:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59556666HCID 59556666, compound

Product 1

HCID 59556702HCID 59556702, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

5-(5-(4-(dimethoxymethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile (0.086 g, 0.227 mmol) and p-toluenesulfonic acid monohydrate (0.043 g, 0.227 mmol) were added in acetone (10 ml) to give a colorless solution. The reaction mixture was heated at 60° C. for 2 hr. The solution was cooled, the reaction mixture was concentrated, the residue was purified via silica gel chromatography (12 g, 50% EtOAc:Heptane) to afford 5-(5-(4-formylphenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile (0.077 g, 0.231 mmol, 102% yield) as white solid.

Workup

  1. customto give a colorless solution
  2. temperatureThe solution was cooled
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was purified via silica gel chromatography (12 g, 50% EtOAc:Heptane)

Sources & evidence

ORD record
ord-9b97b74f61414cea9607bbe69acfba40
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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