Benzene, 1-chloro-4-fluoro- → 1-Benzhydryl-3-(4-chlorophenoxy)azetane

HRID 974538ノート

反応式

HRID 974538 の反応式
[H-].[Na+].[C:3]1([CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=1>CN(C)C=O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:14][CH:12]2[CH2:13][N:10]([CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 178418361HCID 178418361、化合物

生成物 1

HCID 5974941-Benzhydryl-3-(4-chlorophenoxy)azetane収率 82.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

A stirred slurry of 41.3 g (1.03 mole) of 60% sodium hydride (in mineral oil) in 500 ml of dry dimethylformamide under nitrogen atmosphere was heated to 50° C. and 22.5 g (0.94 mole) of 1-diphenylmethyl-3-azetidinol in 700 ml of dry dimethylformamide was added dropwise at a rate which maintained the temperature between 70°-80° C. and allowed a gentle evolution of hydrogen. After the addition was complete, the reaction mixture was stirred for 2 hr at 90° C., then 125 g (0.94 mole) of 1-chloro-4-fluorobenzene was added dropwise. The reaction mixture was stirred at 90° C. under nitrogen for 24 hr, then stirred an additional 24 hr while the reaction mixture cooled to ambient temperature. The reaction mixture was poured into 6 liter of ice water and the solid which formed was collected by filtration to yield 271 g of wet crude product. A sample was recrystallized for elemental analysis from ethanol, yielding a fine tan crystalline product in 82.4% yield, m.p. 113°-114° C.

後処理

  1. temperaturemaintained the temperature between 70°-80° C.
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred at 90° C. under nitrogen for 24 hr
  4. stirringstirred an additional 24 hr while the reaction mixture
  5. temperaturecooled to ambient temperature
  6. customthe solid which formed
  7. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-a59d6d59c0e14d7bab136d1e6e1b0415
出典データセット
uspto-grants-1991_11
特許番号
US05068231

反応ノート

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