p-Toluenesulfonic acid → HCID 22591701, compound

HRID 22840Notes

Reaction equation

HRID 22840 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]23[CH2:17][CH2:16][C:13]([C:18]4[O:19][C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[C:29]([F:32])([F:31])[F:30])=[N:21][N:22]=4)([CH2:14][CH2:15]2)[CH2:12][CH2:11]3)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[F:32][C:29]([F:30])([F:31])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:20]1[O:19][C:18]([C:13]23[CH2:14][CH2:15][C:10]([CH2:9][CH2:8][CH2:7][C:2](=[O:3])[CH3:1])([CH2:11][CH2:12]2)[CH2:17][CH2:16]3)=[N:22][N:21]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 225917112-{4-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl}-5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazole

Product 1

HCID 22591701HCID 22591701, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-{4-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]oct-1-yl }-5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazole (4-G) (0.158 g) was stirred in a mixure of 90% acetone/10% water (20 mL). p-Toluenesulfonic acid (10 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-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo[2.2.2]oct-1-yl)pentan-2-one (4-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-a93cac0300ea415ab08a342745d83c85
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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