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

HRID 2041958노트

반응식

HRID 2041958 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f0c2bbc265c3435f9635c8661fef487f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586571B2

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