Dimethylformamide → 1-(Cyanomethyl)-3-methylenecyclobutanecarbonitrile
Reaction equation
CS(O[CH2:6][C:7]1([C:12]#[N:13])[CH2:10][C:9](=[CH2:11])[CH2:8]1)(=O)=O.[C-]#N.[K+].[CH3:17][N:18](C)C=O>O>[C:17]([CH2:6][C:7]1([C:12]#[N:13])[CH2:10][C:9](=[CH2:11])[CH2:8]1)#[N:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A mixture of (1-cyano-3-methylenecyclobutyl)methyl methanesulfonate (0.41 g, 0.0020 mol) and potassium cyanide (0.66 g, 0.010 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was heated at 65° C. overnight. After diluting with water, the resulting mixture was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and evaporated to dry. The residue was used directly in next step.
Workup
- extractionthe resulting mixture was extracted with EtOAc
- washThe combined organic layers were washed with water, brine
- customdried
- customevaporated
- customto dry
Sources & evidence
- ORD record
- ord-39663aa97586452ca0f4c81c898b239e
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420629B2
Reaction notes
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