Methanol → 2-(4-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)ethanol
Reaktionsgleichung
[CH2:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]=C.ClCCl.[BH4-].[Na+].C[OH:28]>>[C:16]1([C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)=[N:7][NH:8][C:4]=2[CH2:1][CH2:2][OH:28])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Komponenten
Versuchsvorschrift
5-Allyl-4-phenyl-3-p-tolyl-1H-pyrazole (1.0 g, 3.64 mmol) was dissolved in methanol (40 mL) and dichloromethane (10 mL) and cooled to −78° C. on a dry-ice/acetone bath. Ozone was bubbled through the solution for h, until the solution appeared light blue. To the reaction was added sodium borohydride (0.138 g, 3.64 mmol) and the reaction was removed from the dry-ice bath and stirred at room temperature for 1 h. Excess solvent was removed under reduced pressure and the reaction was extracted with EtOAc/H2O, dried over MgSO4, and purified by column chromatography to give the title compound as white solid (0.54 g). LCMS m/z=279.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H), 2.71 (t, J=7.33 Hz, 2H), 3.57 (t, J=7.33 Hz, 2H), 4.65 (bs, 1H), 7.03-7.09 (m, 2H), 7.16-7.23 (m, 3H), 7.24-7.31 (m, 2H), 7.32-7.40 (m, 2H).
Aufarbeitung
- customOzone was bubbled through the solution for h, until the solution
- customthe reaction was removed from the dry-ice bath
- customExcess solvent was removed under reduced pressure
- extractionthe reaction was extracted with EtOAc/H2O
- dry with materialdried over MgSO4
- custompurified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-68c95bb6ada64975a2bbe4bdf90fee40
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09012478B2
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