Dichloromethane → HCID 67168162, 화합물

HRID 1506285노트

반응식

HRID 1506285 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:20]Cl>CO>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14][CH3:20])=[O:13])[C:8]=2[C:15]([F:17])([F:18])[F:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 6344Dichloromethane2회HCID 58374151HCID 58374151, 화합물

생성물 1

HCID 67168162HCID 67168162, 화합물수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 5-phenyl-4-(trifluoromethyl)isoxazole-3-carboxylic acid (Intermediate I-5D, 0.500 g, 1.94 mmol) in dichloromethane (5 mL) and methanol (1 mL) at room temperature was added trimethyldiazomethane (2.0 M in ether) (1.17 mL, 2.33 mmol) slowly over 10 min. During the addition, the solution remained colorless and the evolution of gas nitrogen was noted. Toward the end of the addition, the bubbling ceased and the solution became pale yellow. The reaction mixture was stirred overnight. The reaction mixture was diluted with dichloromethane (40 mL) and washed with brine (20 mL). The aqueous layer was extracted with dichloromethane (2×20 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded methyl 5-phenyl-4-(trifluoromethyl)isoxazole-3-carboxylate (0.509 g, 1.88 mmol, 97% yield) as a yellow oil. The product had an HPLC with a ret. time=2.52 min. (condition A); 1H NMR (400 MHz, CDCl3) δ ppm 4.05 (s, 3H), 7.50-7.64 (m, 3H), and 7.70 (d, J=7.48 Hz, 2H).

후처리

  1. additionDuring the addition
  2. additionToward the end of the addition
  3. washwashed with brine (20 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (2×20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-028cecde7b5a46a4aa2e6062b83c1d20
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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