1,2-Dichloroethane → Methyl 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

HRID 1506520노트

반응식

HRID 1506520 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=[O:26])=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCCl.C(N(CC)CC)C.[C:42]([O:46][CH3:47])(=[O:45])[CH:43]=[CH2:44]>[I-].OCCC1SC=[N+](C)C=1C.CCO>[O:26]=[C:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[C:14]1=[N:15][O:16][C:12]([C:9]3[C:8]([C:27]([F:28])([F:29])[F:30])=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:11][N:10]=3)=[C:13]1[CH2:24][CH2:23]2)[CH2:44][CH2:43][C:42]([O:46][CH3:47])=[O:45]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 7294Methyl Acrylate2회HCID 8471TriethylamineHCID 866698753-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

생성물 1

HCID 67171566Methyl 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate수율 23.76%

시약·촉매·용매 2

HCID 98387703,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodide촉매2회HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

To a mixture of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (Preparation 88A, 80 mg, 0.195 mmol), 5-(2-hydroxyethyl)-3,4-dimethylthiazolium iodide (11.12 mg, 0.039 mmol), 1,2-dichloroethane (1 mL), EtOH (1.000 mL), triethylamine (0.082 mL, 0.585 mmol) and methyl acrylate (0.053 mL, 0.585 mmol) was bubbled with nitrogen for 1 min. and then sealed in a 1-dram vial. The mixture was heated at 75° C. for 15 h. Additional 5-(2-hydroxyethyl)-3,4-dimethylthiazolium iodide (30 mg) and methyl acrylate (0.053 mL, 0.585 mmol) were added and the mixture was stirred at 75° C. for 7 h. The solvents were removed under reduced pressure. The residue was treated with water (2 mL) and extracted with dichloromethane. The combined dichloromethane extracts were dried (sodium sulfate) and concentrated. Flash chromatography purification (4 g silica gel column, 20→100% dichloromethane in heptanes) afforded methyl 4-oxo-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (23 mg, 0.046 mmol, 23.76% yield) as a glassy solid.

후처리

  1. customwas bubbled with nitrogen for 1 min.
  2. customsealed in a 1-dram vial
  3. customThe solvents were removed under reduced pressure
  4. additionThe residue was treated with water (2 mL)
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried (sodium sulfate)
  7. concentrationconcentrated
  8. customFlash chromatography purification (4 g silica gel column, 20→100% dichloromethane in heptanes)

출처 및 근거

ORD 기록
ord-ea3881b06a4f4ee68e2fa37e69d06f77
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

반응 노트

불러오는 중…