Methyl Acrylate → Methyl 3-[3-(trifluoromethyl)phenyl]4,5-dihydroisoxazole-5-carboxylate

HRID 1025763노트

반응식

HRID 1025763 반응식
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17]>C(Cl)Cl>[F:11][C:10]([F:13])([F:12])[C:6]1[CH:5]=[C:4]([C:3]2[CH2:17][CH:16]([C:15]([O:19][CH3:20])=[O:18])[O:1][N:2]=2)[CH:9]=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 7294Methyl AcrylateHCID 85444714HCID 85444714, 화합물

생성물 1

HCID 57803314Methyl 3-[3-(trifluoromethyl)phenyl]4,5-dihydroisoxazole-5-carboxylate수율 105.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a flask containing N-hydroxy-3-(trifluoromethyl)benzenecarboximidoyl chloride (2.0 g, 8.9 mmol) and methyl acrylate (0.7 g, 8 mmol) in methylene chloride (100 mL) at 0° C. under an inert atmosphere was added TEA (0.90 g, 8.8 mmol). The reaction mixture was slowly warmed to ambient temperature, stirred for 20 h, quenched with water (30 mL), and extracted with methylene chloride (2×50 mL). The organic extracts were combined, washed with saline solution (50 mL), dried over sodium sulfate, concentrated in vacuo, and chromatographed on silica gel, eluting with methylene chloride/methanol (100/1 to 95/5). The appropriate fractions were combined and concentrated in vacuo to give methyl 3-[3-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole-5-carboxylate (2.3 g, 100%): LCMS: 274.2 (M+H+, 100%); 1H NMR: (CDCl3) δ 8.03 (s, 1H), 7.92 (d, 1H), 7.71 (d, 1H), 7.59 (dd, 1H), 5.28 (dd, 1H), 3.86 (s, 3H), 3.71 (dd, 2H).

후처리

  1. customquenched with water (30 mL)
  2. extractionextracted with methylene chloride (2×50 mL)
  3. washwashed with saline solution (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel
  7. washeluting with methylene chloride/methanol (100/1 to 95/5)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-564410f87e0249869bcb4c2b663491b5
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729063B2

반응 노트

불러오는 중…