Triethylamine → Methyl 4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)-2-methylbenzoate

HRID 1037015노트

반응식

HRID 1037015 반응식
Cl[C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1.[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([C:25]([F:28])([F:27])[F:26])=[CH2:24])[CH:20]=[C:19]([Cl:29])[C:18]=1[Cl:30].CCN(CC)CC.CC(=O)OCC>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[C:21]([C:23]2([C:25]([F:28])([F:27])[F:26])[O:15][N:14]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=3)[CH2:24]2)[CH:20]=[C:19]([Cl:29])[C:18]=1[Cl:30]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86685465Methyl 4-(chloro(hydroxyimino)methyl)-2-methylbenzoate

생성물 1

HCID 86685464Methyl 4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)-2-methylbenzoate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 4-(chloro(hydroxyimino)methyl)-2-methylbenzoate (12.6 mmol) in DMF (30 mL) at 0° C. was added 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.2 g, 15.1 mmol) followed by Et3N (2.55 g, 25.2 mmol). The reaction mixture was stirred at rt for 18 h, poured into ice-water (30 mL) and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (10:1) to give methyl 4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)-2-methylbenzoate (4.1 g; yield 70% over 3 steps) as a pale yellow oil. 1H NMR (500 MHz, CDCl3): δ 7.98 (d, J=8.5 Hz, 1H), 7.66 (s, 2H), 7.55 (s, 2H), 4.13 (d, J=17.5 Hz, 1H), 3.93 (s, 3H), 3.73 (d, J=17.5 Hz, 1H), 2.64 (s, 3H) ppm; MS: m/z=465.9 (M+1, ESI+).

후처리

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE

출처 및 근거

ORD 기록
ord-2f2f6c672c4b40ac9e9a0d2782a46086
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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