Isobutyronitrile → HCID 67125680, compound

HRID 645477Notes

Reaction equation

HRID 645477 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]1

Participants

5

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

  1. stirringThe mixture is stirred at room temperature for 13 h
  2. customthe reaction is quenched by the addition of aq. NH4Cl
  3. extractionThe mixture is extracted with ether
  4. washthe combined organic extracts are washed with H2O and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18fd92b01be148c8ac655840502ebbf2
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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