Ethyl Bromide → 2-(2,5-Dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone

HRID 1387330ノート

反応式

HRID 1387330 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].[CH3:22][C:23]1[CH:27]=[C:26]([C:28](Cl)=[O:29])[O:25][N:24]=1.[Cl-].[NH4+]>C1COCC1>[CH3:22][C:23]1[CH:27]=[C:26]([C:28]([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:29])[O:25][N:24]=1

参加物

7

反応物 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 109462162-Bromobenzyl-(2,5-dimethylphenyl)etherHCID 129050993-Methyl-1,2-oxazole-5-carbonyl chloride

生成物 1

HCID 226246042-(2,5-Dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone収率 17.4%

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-methylisoxazol-5-carbonyl chloride (1.45 g, 0.01 mol) and THF (15 ml) at −70 to −60° C. over 15 minutes, and then the mixture was stirred at −70 to −60° C. for 0.5 hours. After completion of the reaction, saturated aqueous ammonium chloride solution (150 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 3-methylisoxazol-5-yl ketone (0.56 g, 17.4%) as colorless crystals. mp. 106-108° 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 −70 to −60° C. for 0.5 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-f4c5f267b56f4cfe9d1a74de9ec8e409
出典データセット
uspto-grants-2001_07
特許番号
US06268312B1

反応ノート

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