Potassium Carbonate → 5,5-Dimethyl-3-(5-methyl-3-trifluoromethylisoxazol-4-ylmethylthio)-2-isoxazoline

HRID 1172081ノート

反応式

HRID 1172081 の反応式
O.[SH-].[Na+].[CH3:4][C:5]1([CH3:14])[O:9][N:8]=[C:7]([S:10]([CH3:13])(=O)=O)[CH2:6]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:29]1[C:30]([C:35]([F:38])([F:37])[F:36])=[N:31][O:32][C:33]=1[CH3:34]>CN(C)C=O.O>[CH3:4][C:5]1([CH3:14])[O:9][N:8]=[C:7]([S:10][CH2:13][C:29]2[C:30]([C:35]([F:38])([F:37])[F:36])=[N:31][O:32][C:33]=2[CH3:34])[CH2:6]1

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 16211346Sodium hydrosulfide hydrateHCID 178628854-Bromomethyl-5-methyl-3-trifluoromethylisoxazoleHCID 23689980Sodium Formaldehyde Sulfoxylate

生成物 1

HCID 178628475,5-Dimethyl-3-(5-methyl-3-trifluoromethylisoxazol-4-ylmethylthio)-2-isoxazoline収率 75.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

0.4 g of sodium hydrosulfide hydrate (purity: 70%, 4.6 mmoles) was added to a solution of 0.4 g (2.3 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred for 2 hours. Thereto were added 0.3 g (2.3 mmoles) of potassium carbonate, 0.4 g (2.3 mmoles) of Rongalit and 0.5 g (1.8 mmoles) of 4-bromomethyl-5-methyl-3-trifluoromethylisoxazole. The resulting mixture was stirred at room temperature for 14 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.4 g (yield: 70.0%) of 5,5-dimethyl-3-(5-methyl-3-trifluoromethylisoxazol-4-ylmethylthio)-2-isoxazoline.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 14 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

出典と根拠

ORDレコード
ord-b55cc2a0a9a34ff88a2a62c4a35d4acc
出典データセット
uspto-grants-2010_11
特許番号
US07833939B2

反応ノート

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