Chlorosuccinimide → 5-((2,6-Difluorobenzyloxy)methyl)-5-methyl-3-(2-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole

HRID 58945

反応式

HRID 58945 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH:5]=[N:6][OH:7].ClN1C(=O)CCC1=O.C([O-])(O)=O.[Na+].[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=1[CH2:35][O:36][CH2:37][C:38]([CH3:40])=[CH2:39]>ClCCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.CN(C)C=O>[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=1[CH2:35][O:36][CH2:37][C:38]1([CH3:40])[O:7][N:6]=[C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:12])([F:13])[F:1])[CH2:39]1

参加物

9

反応物 4

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 16173382-(Trifluoromethyl)benzenecarbaldehyde oximeHCID 112640711,3-Difluoro-2-((2-methylallyloxy)methyl)benzene

生成物 1

HCID 894918555-((2,6-Difluorobenzyloxy)methyl)-5-methyl-3-(2-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole収率 90.2%

試薬・触媒・溶媒 4

HCID 67553Tetrabutylammonium Iodide触媒HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

223 mg of 2-trifluoromethylbenzaldehyde oxime was dissolved in 4 mL of 1,2-dichloroethane, and then, 230 mg of N-chlorosuccinimide and 0.4 mL of dimethylformamide were slowly added thereto at a temperature of 0° C. The reaction mixture was stirred at room temperature for 1 hour, and then, the reaction state was confirmed by TLC. When the oxime, which was a starting material, disappeared, the reaction mixture was cooled to a temperature 0° C., and then, 182 mg of NaHCO3, 27 mg of tetrabutylammonium iodide, and 342 mg of 1,3-difluoro-2-((2-methylallyloxy)methyl)benzene were sequentially, slowly added thereto. The reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane, and then, washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 410 mg of 5-((2,6-difluorobenzyloxy)methyl)-5-methyl-3-(2-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole.

後処理

  1. customat a temperature of 0° C
  2. temperaturethe reaction mixture was cooled to a temperature 0° C.
  3. additionslowly added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. washwashed with water
  6. customthe obtained organic layer was dried
  7. concentrationconcentrated
  8. customthe concentrate was separated by silicagel column chromatography

出典と根拠

ORDレコード
ord-9c97f89873f34a5c9abe1bf60c7ee372
出典データセット
uspto-grants-2016_09
特許番号
US09439432B2

関連ノート

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