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

HRID 1025763ノート

反応式

HRID 1025763 の反応式
[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

参加物

4

反応物 2

HCID 7294Methyl AcrylateHCID 85444714HCID 85444714、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-564410f87e0249869bcb4c2b663491b5
出典データセット
uspto-grants-2014_05
特許番号
US08729063B2

反応ノート

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