Isobutyronitrile → HCID 67125680, compound
Reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].[Li+].CC([N-]C(C)C)C.Br[CH2:15][CH:16]1[CH2:18][CH2:17]1>C1COCC1>[CH:18]1([CH2:17][C:2]([CH3:4])([CH3:3])[C:1]#[N:5])[CH2:16][CH2:15]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of isobutyronitrile (29 mmol) in THF (60 mL) is added LDA (2 M in THF, 35 mmol) at −78° C. After stirring at −78° C. for 2 h, to this solution is added bromomethyl cyclopropane (32 mmol) at −78° C. The mixture is stirred at room temperature for 13 h, and then the reaction is quenched by the addition of aq. NH4Cl. The mixture is extracted with ether, and the combined organic extracts are washed with H2O and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give 3-cyclopropyl-2,2-dimethylpropionitrile, which is directly used for the next reaction without further purification.
Workup
- stirringThe mixture is stirred at room temperature for 13 h
- customthe reaction is quenched by the addition of aq. NH4Cl
- extractionThe mixture is extracted with ether
- washthe combined organic extracts are washed with H2O and brine
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-18fd92b01be148c8ac655840502ebbf2
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07704996B2
Reaction notes
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