Reaktionsgleichung
[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>>[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3].[C:1]([C:5]1[NH:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Komponenten
Versuchsvorschrift
Methyl 5-tert-butyl-3-nitropyrrole-2-carboxylate was prepared as described in Method N-1 Step 3. To a solution of methyl 5-tert-butyl-3-nitropyrrole-2-carboxylate (10.38 g, 45.9 mmol) in a THF—MeO—H2O mixture(1.0:1.0:0.5, 250 mL) at room temp. was added a 1N NaOH solution (92 mL, 92 mmol) via pippette. The color of the reaction mixture turned from green to red. The mixture was warmed to the reflux temperature, maintained for 3 hr, cooled to room temp. and concentrated in vacuo. The residue was made acidic using a 10% citric acid solution and was extracted with EtOAc (2×50 mL). The organic layer was washed with a saturated NaCl solution, dried (MgSO4), and concentrated in vacuo. The residue was triturated with hexanes to give 5-tert-butyl-3-nitropyrrole-2-carboxylic acid (9.70 g, 99%) as a green powder: 1H NMR (DMSO-d6) δ1.24 (s, 9H), 6.41 (d, J=2.9 Hz, 1H), 12.19 (br s, 1H), 13.50 (br s, 1H).
Aufarbeitung
- temperatureThe mixture was warmed to the reflux temperature
- temperaturemaintained for 3 hr
- temperaturecooled to room temp.
- concentrationconcentrated in vacuo
- extractionwas extracted with EtOAc (2×50 mL)
- washThe organic layer was washed with a saturated NaCl solution
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was triturated with hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-718554d7922b45aba6566e78f27e329d
- Quelldatensatz
- uspto-grants-2002_02
- Patentnummer
- US06344476B1
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