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

HRID 1387357ノート

反応式

HRID 1387357 の反応式
[Mg].BrCC.Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.CON(C)[C:23]([C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1)=[O:24]>O.C1COCC1>[CH3:30][C:27]1[CH:26]=[C:25]([C:23]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[O:24])[O:29][N:28]=1

参加物

7

反応物 4

HCID 6332Ethyl BromideHCID 53150262-[(2-Bromophenyl)methoxy]oxaneHCID 5462224MagnesiumHCID 45099368N-Methoxy-N,3-dimethylisoxazole-5-carboxamide

生成物 1

HCID 226246602-(2-Tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone収率 67.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
55 °C

実験手順

Magnesium (0.73 g, 0.03 mol) and bromoethane (0.2 ml) were added to a mixture of 1-bromo-2-(2-tetrahydro-pyranyloxymethyl)benzene (5.42 g, 0.02 mol) and THF (50 ml) under an atmosphere of nitrogen gas, and the resulting mixture was stirred at 50 to 60° C. for 1 hour to prepare Grignard reagent. The Grignard reagent was added dropwise to a mixture of N-methoxy-3, N-dimethyl-5-isoxazolcarboxamide (3.40 g, 0.02 mol) and THF (40 ml). The mixture was stirred at −60° C. to room temperature for 1 hour, water (200 ml) was added, and the mixture was extracted with ether (200 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2-tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone (4.09 g, yield: 67.9%) as a colorless oil.

後処理

  1. stirringThe mixture was stirred at −60° C. to room temperature for 1 hour
  2. extractionthe mixture was extracted with ether (200 ml)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

出典と根拠

ORDレコード
ord-c9c76aefc0fa42b1b3e7b69bf98e8950
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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