Water → 2-Methyl-2-phenylbutanenitrile

HRID 2106045Notes

Reaction equation

HRID 2106045 reaction equation
[C:1]1([CH:7]([CH3:10])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:21](I)[CH3:22].O>CS(C)=O.C1COCC1>[CH3:10][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:21][CH3:22])[C:8]#[N:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 157612-PhenylpropionitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 32541802-Methyl-2-phenylbutanenitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5 g (38 mmol) of 2-phenylpropionitrile in 50 mL of DMSO was added 42 mL of a 1M solution of NaHMDS in THF. After 15 minutes, the reaction was cooled to 0° C. and 4.6 mL of ethyl iodide was added. The reaction was monitored by TLC. After 30 minutes, the mixture was poured into water and extracted with diethyl ether. The combined organics were washed with four portions of water, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6.1 g of 2-methyl-2-phenylbutyronitrile as an oil.

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with diethyl ether
  3. washThe combined organics were washed with four portions of water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0db3792bfa244f2ab0afeab0999fcea7
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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