Sulfuric Acid → 2-(2,5-Dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone

HRID 1004353ノート

反応式

HRID 1004353 の反応式
BrCC.[Mg].Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21].[C:22]([C:24]1[CH:28]=[CH:27][O:26][N:25]=1)#N.S(=O)(=O)(O)[OH:30]>C1COCC1>[O:26]1[CH:27]=[CH:28][C:24]([C:22]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[O:30])=[N:25]1

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 109462162-Bromobenzyl-(2,5-dimethylphenyl)etherHCID 226246101,2-Oxazole-3-carbonitrile

生成物 1

HCID 109028752-(2,5-Dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone収率 6.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
50 °C

実験手順

THF (2 ml) and bromoethane (0.1 ml) were added to magnesium (0.49 g, 0.02 mol) in a stream of nitrogen, and the mixture was stirred at 50° C. for 10 minutes. Then, a mixture of 1-bromo-2-(2,5-dimethylphenoxymethyl)benzene (2.91 g, 0.01 mol) and THF (8 ml) was added at 50 to 60° C. over 30 minutes, and the mixture was stirred at 50 to 60° C. for 1 hour. After completion of the reaction, the reaction mixture was added to a mixture of 3-cyanoisoxazole (1.45 g, 0.015 mol) and THF (15 ml) at 20° C. or lower over 15 minutes, and then the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 2N sulfuric acid (200 ml) was added, and the mixture was extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.20 g, 6.3%) as colorless crystals. mp. 90.5-92° C.

後処理

  1. additionwas added at 50 to 60° C. over 30 minutes
  2. stirringthe mixture was stirred at 50 to 60° C. for 1 hour
  3. customAfter completion of the reaction
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. additionwas added
  6. extractionthe mixture was extracted with ether
  7. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  10. customrecrystallized from n-hexane

出典と根拠

ORDレコード
ord-a6076fd13f3a420c896db08a2fa0ad7e
出典データセット
uspto-grants-2000_04
特許番号
US06048885

反応ノート

読み込み中…