Water → 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4H-chromeno[4,3-c]isoxazole-7-carbaldehyde

HRID 1506442노트

반응식

HRID 1506442 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[CH:18]=[CH:19][C:20]([CH:25]=C)=[CH:21][C:22]=5[O:23][CH2:24][C:13]=34)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:35]CC1.I([O-])(=O)(=O)=O.[Na+].O>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[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[CH:18]=[CH:19][C:20]([CH:25]=[O:35])=[CH:21][C:22]=5[O:23][CH2:24][C:13]=34)[C:8]=2[C:27]([F:28])([F:30])[F:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 671678993-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4H-chromeno[4,3-c]isoxazole

생성물 1

HCID 866699093-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4H-chromeno[4,3-c]isoxazole-7-carbaldehyde수율 95%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4H-chromeno[4,3-c]isoxazole (Preparation 62G, 0.060 g, 0.146 mmol) and a 50% aqueous solution of NMO (0.030 mL, 0.146 mmol) at room temperature was added a 4% aqueous solution of osmium tetroxide (0.046 mL, 5.85 μmol). The reaction mixture was stirred at room temperature for 5 h. The intermediate diol had an HPLC ret. time=3.09 min and an LCMS M+1=445.0. Sodium periodate (0.047 g, 0.219 mmol) was added to the homogeneous mixture followed by water (0.10 mL), and the reaction was stirred for 60 min. at room temperature. Concentration under reduced pressure afforded a tan solid residue that was then diluted with ethyl acetate (40 mL), washed with the water (10 mL), and washed with brine (10 mL). The organic layer was collected, and the aqueous layer was washed with ethyl acetate (40 mL). The combined organic layers were dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4H-chromeno[4,3-c]isoxazole-7-carbaldehyde (0.057 g, 0.138 mmol, 95% yield) as a pale yellow solid. The product had an HPLC ret. time=3.49 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA.

후처리

  1. stirringthe reaction was stirred for 60 min. at room temperature
  2. concentrationConcentration under reduced pressure
  3. customafforded a tan solid residue that
  4. washwashed with the water (10 mL)
  5. washwashed with brine (10 mL)
  6. customThe organic layer was collected
  7. washthe aqueous layer was washed with ethyl acetate (40 mL)
  8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  9. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-14ef1df245d5491cac60f2977c59e9d9
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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