Ethanol → Ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate

HRID 646006

반응식

HRID 646006 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[CH:20]1([C:24](=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:22][CH2:21]1.[O-]CC.[Na+].C(O)C>CN(C=O)C.O1CCCC1.O>[CH:20]1([C:24]2[O:6][N:5]=[C:4]([C:3]3[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:11])[C:25]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:22][CH2:23]1

참가 물질

9

반응물 5

HCID 702EthanolHCID 31398ChlorosuccinimideHCID 91328Benzaldehyde, 2,6-dichloro-, oximeHCID 2723922Sodium ethoxideHCID 21846412Ethyl 3-cyclobutyl-3-oxopropanoate

생성물 1

HCID 59264874Ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate수율 38%

시약·촉매·용매 3

HCID 962Water용매3회HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2,6-dichlorobenzaldehyde oxime (2.2 g, 11.6 mmol) in N,N,-dimethylformamide (7 mL) cooled in a water bath was added solid N-chlorosuccinimide (1.5 g, 11.6 mmol). The solution was stirred with the flask in the water bath for approximately 20 minutes and then with the flask out of the bath for approximately 1 hour. The solution was poured into water and then extracted twice with ether. The combined organic phases were dried over magnesium sulfate and concentrated. To a separate solution of ethyl 3-cyclobutyl-3-oxopropanoate (2.4 g, 13.9 mmol) in tetrahydrofuran (3 mL) at 0° C. was added a 3.16 M solution of sodium ethoxide in ethanol (4.4 mL, 13.9 mmol) quickly. The solution was stirred for a few minutes. To that solution was added the isolated imidoyl chloride in tetrahydrofuran (5 mL) dropwise. The solution was stirred at 0° C. for approximately 1 h and then allowed to stir at ambient temperature overnight. The solution was poured into water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution) to afford a white solid (1.5 g, 38%). 1H-NMR (DMSO-d6) δ 7.63-7.53 (m, 3H), 4.25 (quintet, J=9 Hz, 1H), 4.02 (q, J=7 Hz, 2H), 2.43-2.36 (m, 4H), 2.15-1.89 (m, 2H), 0.94 (t, J=7 Hz, 3H).

후처리

  1. extractionextracted twice with ether
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated
  4. stirringThe solution was stirred at 0° C. for approximately 1 h
  5. stirringto stir at ambient temperature overnight
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution)

출처 및 근거

ORD 기록
ord-b56950cc4b0946b6af12eb34fae074df
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705028B2

연결된 노트

불러오는 중…