Water → Isoxazole, 4,5-dihydro-5,5-dimethyl-3-[(phenylmethyl)thio]-

HRID 1760146ノート

反応式

HRID 1760146 の反応式
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH2:20][C:19]([CH3:22])([CH3:21])[O:18][N:17]=1.O>CN(C)C=O>[CH2:1]([S:8][C:16]1[CH2:20][C:19]([CH3:22])([CH3:21])[O:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 116654173-Chloro-5,5-dimethyl-4,5-dihydro-1,2-oxazole

生成物 1

HCID 12137651Isoxazole, 4,5-dihydro-5,5-dimethyl-3-[(phenylmethyl)thio]-収率 62.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2.8 g (22.5 mmoles) of benzylmercaptan dissolved in 50 ml of dimethylformamide were added, in a nitrogen current, 3.2 g (23.2 mmoles) of anhydrous potassium carbonate and 3.0 g (22.5 mmoles) of 3-chloro-5,5-dimethyl-2-isoxazoline. The mixture was stirred at 100° C. for 2 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 water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, and the residue was purified by silica gel column chromatography to obtain 3.1 g (yield: 62.0%) of 3-benzylthio-5,5-dimethyl-2-isoxazoline as a yellow oily substance (refractive index nD20=1.5521).

後処理

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-00ebf6a41ae44654a9f2430f70939c63
出典データセット
uspto-grants-2005_01
特許番号
US06841519B1

反応ノート

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