Potassium Permanganate → 1-tert-butyl-1H-pyrrole-3-carboxylic acid
Reaction equation
[C:1]([N:5]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[O-:12][Mn](=O)(=O)=O.[K+].OS([O-])=O.[Na+]>CC(C)=O.CC(C)=O.O>[C:1]([N:5]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]Participants
6
Procedure
To a solution of 1-tert-butyl-1H-pyrrole-3-carbaldehyde (0.339 g, 2.24 mmol) in acetone (40 mL) was added, over a 2 h period, a solution of KMnO4 (0.708 g, 4.48 mmol) in Acetone/H2O (1:1, 60 mL). After 3 h, the reaction was poured into a solution of 10% NaHSO3/1N HCl (120 mL) and the solution was extracted with DCM (3×60 mL). The combined extracts were washed with H2O (2×60 mL) and 5% NaHCO3 (3×60 mL). The bicarbonate washes were carefully acidified to pH 3 and extracted with DCM (3×60 mL). The combined organic layers were washed with brine (1×), dried (MgSO4) and concentrated afford 1-tert-butyl-1H-pyrrole-3-carboxylic acid (0.270 g, 72% yield) as a white solid. MS (ESI) m/z: 168.1 (M+H+).
Workup
- extractionthe solution was extracted with DCM (3×60 mL)
- washThe combined extracts were washed with H2O (2×60 mL) and 5% NaHCO3 (3×60 mL)
- extractionextracted with DCM (3×60 mL)
- washThe combined organic layers were washed with brine (1×)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1851086dcc6e4dadb7e2ce9eac0cc3ec
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143293B2
Reaction notes
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