Acetone → 3-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrile
Reaction equation
[C:1]([OH:6])(=O)[C:2](O)=O.[C:7]([C:9]1([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)OC(CCC(C)C)CO1)#[N:8].[C:29](=O)([O-])[O-].[K+].[K+].[CH3:35][C:36]([CH3:38])=O>O>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:9]([CH:36]([CH3:38])[CH3:35])([CH2:29][CH2:2][CH:1]=[O:6])[C:7]#[N:8])[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
Oxalic acid dehydrate (504.6 mg, 3.96 mmol) was added to a solution of the acetal (19) (372 mg, 1.16 mmol) in acetone (10 mL) and water (10 mL). The resulting mixture was stirred at 80° C. for four hours. The reaction mixture was cooled to room temperature. Potassium carbonate (1.3 g) was added to quench the reaction. The mixture was extracted with ethyl ether (3×20 mL). The organic solution was washed with brine, dried over sodium sulfate, concentrated to afford the crude product (17) (293 mg), which was used in the next step without further purification. The product was confirmed by 1H-NMR spectra.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customto quench
- customthe reaction
- extractionThe mixture was extracted with ethyl ether (3×20 mL)
- washThe organic solution was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8e15abe2e51e4aeaa373318080326d13
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748648B2
Reaction notes
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