Diethyl Oxalate → 3-Cyano-2-oxotridecanoic acid ethyl ester
Reaction equation
[CH2:1]([C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH:1]([C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.5 Moles of n-undecyl cyanide and 0.5 moles of diethyl oxalate are mixed in 1,000 ml of dimethylformamide. To this solution is added with ice cooling 0.52 moles of potassium t-butoxide. The mixture is allowed to stir overnight at room temperature. Following evaporation (rotary evaporator under vacuum) of most of the dimethylformamide the residue is mixed with 3 liters of diethyl ether followed by the addition of 1 liter water. The mixture is acidified with concentrated hydrochloric acid to a pH of 3 and then the ether phase is separated. After washing the ether with water and drying the ether over magnesium sulfate evaporation of the ether affords 3-cyano-2-oxotridecanoic acid ethyl ester. Recrystallization from petroleum ether at 30°-60° C. provides pure material.
Workup
- customevaporation (rotary evaporator under vacuum) of most of the dimethylformamide the residue
- additionis mixed with 3 liters of diethyl ether
- additionfollowed by the addition of 1 liter water
- customthe ether phase is separated
- washAfter washing the ether with water
- dry with materialdrying the ether
- customover magnesium sulfate evaporation of the ether
Sources & evidence
- ORD record
- ord-e3d5a5a442f9490e9a1780403e9bfd39
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04428959
Reaction notes
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