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

HRID 2041958

反応式

HRID 2041958 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f0c2bbc265c3435f9635c8661fef487f
出典データセット
uspto-grants-2013_11
特許番号
US08586571B2

関連ノート

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