2-Tert-Butylphenol → 1-Benzhydryl-3-(2-tert-butylphenoxy)azetidine

HRID 2041958Notes

Reaction equation

HRID 2041958 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](CS([O-])(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:7]([N:8]1[CH2:11][CH:10]([O:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:23]([CH3:26])([CH3:24])[CH3:25])[CH2:9]1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 69232-Tert-ButylphenolHCID 14798Sodium HydroxideHCID 71431707(1-Benzhydrylazetidin-3-yl)methanesulfonate

Product 1

HCID 595771511-Benzhydryl-3-(2-tert-butylphenoxy)azetidineYield 66%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 1-(diphenylmethyl)-3-azetidinylmethane sulfonate (12.68 g, 39.9 mmol), 2-tert-butylphenol (6.0 g, 39.9 mmol), tetrabutylammonium bromide (1.29 g, 3.99 g) and sodium hydroxide (15.0 mL of 8.0 M solution in water, 120 mmol) in toluene (40 mL) was heated at 100° C. for 5 h. Then, the reaction mixture was cooled to room temperature, diluted with ethyl acetate and separated. The organic layer was washed with water, saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 100:0 to 98:2 heptane/ethyl acetate) provided impure 1-benzhydryl-3-(2-tert-butylphenoxy)azetidine (9.10 g, 66%) as a yellow oil, which was used without further purification or characterization.

Workup

  1. customseparated
  2. washThe organic layer was washed with water, saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica gel, 100:0 to 98:2 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-f0c2bbc265c3435f9635c8661fef487f
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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