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

HRID 58945노트

반응식

HRID 58945 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c97f89873f34a5c9abe1bf60c7ee372
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439432B2

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