Ethylene Glycol → 3-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine

HRID 70572ノート

反応式

HRID 70572 の反応式
[CH2:1]([OH:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2([CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[O:4][CH2:1][CH2:2][O:3]2)=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate2 回HCID 128598381-(4-Bromophenyl)-4-(diethylamino)butan-1-one

生成物 1

HCID 584524843-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine収率 91%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

Ethylene glycol (10 mL) and p-toluenesulfonic acid monohydrate (128 mg) were added to a solution of 1-(4-bromophenyl)-4-(diethylamino)butan-1-one (2.0 g) in toluene (80 mL), and the mixture was stirred at 150° C. for one hour. The reaction solution was cooled to room temperature and p-toluenesulfonic acid monohydrate (1.28 g) was added, after which the mixture was stirred at 150° C. for further one hour. The reaction solution was cooled to room temperature and neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound as a brown oil (2.09 g, 91%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringafter which the mixture was stirred at 150° C. for further one hour
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-d04b8a6eb8924dedad28ee4afc3226fb
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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