Iodoethane → 4-(1-Cyano-1-ethylpropyl)benzonitrile

HRID 419977Notes

Reaction equation

HRID 419977 reaction equation
[C:1]([CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)#[N:2].[CH2:12](I)[CH3:13].[H-].[Na+].[CH3:17][CH2:18]OC(C)=O>CCCCCCC.O.CN(C=O)C>[C:1]([C:3]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([CH2:12][CH3:13])[CH2:17][CH3:18])#[N:2]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1366864-Cyanophenylacetonitrile

Product 1

HCID 582984684-(1-Cyano-1-ethylpropyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Cyanomethylbenzonitrile (1.02 g, 7.18 mmol) and ethyl iodide (2.25 g, 14.4 mmol) are added to DMF (20.0 mL), and the resulting solution is cooled to 0° C. NaH (576 mg, 14.4 mmol) is added in portions. The mixture is warmed to room temperature and then stirred for 3 hours. Water (100 mL) is added, and the aqueous phase is extracted with EtOAc (4 times with 50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by Combi-Flash silica gel chromatography, eluting with mixtures of heptane and EtOAc (100/0 to 70/30), (936 mg, 5.51 mmol, 77%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.42 Hz, 6H) 1.89-2.14 (m, 4H) 7.64 (d, J=8.40 Hz, 2H) 7.92 (d, J=8.59 Hz, 2H).

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. extractionthe aqueous phase is extracted with EtOAc (4 times with 50.0 mL)
  3. dry with materialThe combined organic phases are dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on the rotovaporator
  6. customThe product is purified by Combi-Flash silica gel chromatography

Sources & evidence

ORD record
ord-10ba435c4cd842f48206c1b80667c273
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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