p-Toluenesulfonic acid → 1-Benzhydryl-3-(2,4,4'-trichlorobenzhydryloxy)azetidine

HRID 1785629Notes

Reaction equation

HRID 1785629 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:29]([N:42]1[CH2:45][CH:44](O)[CH2:43]1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH:29]([N:42]1[CH2:45][CH:44]([O:12][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[C:3]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:2]=2[Cl:1])[CH2:43]1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 225654352,4,4'-Trichlorobenzhydrol

Product 1

HCID 689038181-Benzhydryl-3-(2,4,4'-trichlorobenzhydryloxy)azetidineYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,4,4′-trichlorobenzhydrol (2) (174 mmol), p-toluenesulfonic acid (174 mmol) and 1-benzhydryl-3-azetidinol (1) (87 mmol) in toluene (700 mL) was heated at reflux under Dean-Stark conditions for 30 minutes. The solution was cooled, washed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography [SiO2; (10% ethyl acetate:isohexane)] to furnish the product as a yellow oil (22.0 g, 50%).

Workup

  1. temperatureat reflux under Dean-Stark conditions for 30 minutes
  2. temperatureThe solution was cooled
  3. washwashed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography [SiO2; (10% ethyl acetate:isohexane)]

Sources & evidence

ORD record
ord-a35001a2ca2e4f4a9f08929975dd943e
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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