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

HRID 1004381노트

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HRID 1004381 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
55 °C

실험 절차

Magnesium (0.73 g, 0.03 mol) and bromoethane (0.2 ml) were added to a mixture of 1-bromo-2-(2-tetrahydropyranyloxymethyl)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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3cb960f3788c4b6d8c979270384d3f69
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048885

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