Reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][O:11][CH2:10]1.C(=O)([O-])O.[Na+]>C1COCC1>[C:5]([CH:4]([C:3]#[N:7])[C:9]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][O:11][CH2:10]1)#[N:6]Participants
6
Procedure
440 mg (11.00 mmol) of sodium hydride (60% in mineral oil) were initially charged in 30 ml of THF, and 726 mg (11.00 mmol) of malononitrile were added in portions. Thereafter, 2.3 g (11.00 mmol) of the compound obtained in example 11A in THF (50 ml) were added. The mixture was stirred at RT for 6 h and then heated to 50° C. overnight. After cooling, the mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate, filtered and concentrated. The residue (2.66 g) was dried under high vacuum for 1 h and then converted without further purification.
Workup
- temperatureheated to 50° C. overnight
- temperatureAfter cooling
- extractionextracted three times with ethyl acetate
- washThe combined organic phases were washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- dry with materialThe residue (2.66 g) was dried under high vacuum for 1 h
- customconverted without further purification
Sources & evidence
- ORD record
- ord-9e968955856e4e3fabd83b50d7d5a609
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765769B2
Linked notes
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