p-Toluenesulfonic acid → HCID 22591679, compound

HRID 1784494Notes

Reaction equation

HRID 1784494 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][CH2:24][CH2:25][C:26]4([CH3:31])OCC[O:27]4)([CH2:19][CH2:20]2)[CH2:17][CH2:16]3)=[N:13][N:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]([C:15]23[CH2:22][CH2:21][C:18]([CH2:23][CH2:24][CH2:25][C:26](=[O:27])[CH3:31])([CH2:19][CH2:20]2)[CH2:17][CH2:16]3)=[N:13][N:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 225916872-(2-Chloro-4-methoxyphenyl)-5-{4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-1,3,4-oxadiazole

Product 1

HCID 22591679HCID 22591679, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-Chloro-4-methoxyphenyl)-5-{4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-1,3,4-oxadiazole (5-G) (0.200 g) was stirred in a mixure of 90% acetone/10% water (20 mL). p-Toluenesulfonic acid (15 mg) was added to the solution. The reaction was heated to reflux for 1 h. The volume was reduced by evaporation of acetone in vacuo. The mixture was then layered with ethyl acetate (25 mL) and saturated sodium bicarbonate solution (25 mL). The ethyl acetate layer was extracted and dried (MgSO4). Solvent was removed in vacuo to afford pure 5-{4-[5-(2-chloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one (5-H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 h
  3. customThe volume was reduced by evaporation of acetone in vacuo
  4. extractionThe ethyl acetate layer was extracted
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-58f158a836644cc2bae7cfd18667abfe
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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