Iodoethane → 2,2-Diethylmalononitrile

HRID 12475

Reaction equation

HRID 12475 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](I)[CH3:7].[CH3:9][C:10]([O-])(C)C.[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:9]([C:2]([CH2:6][CH3:7])([C:1]#[N:5])[C:3]#[N:4])[CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8010MalononitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 27772312,2-Diethylmalononitrile

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Malononitrile (15.2 g) was mixed with TBAB (3.0 g, 4 mol %) and ethyl iodide (36.8 mL, 2 equiv.). After stirring for 30 minutes at room temperature, the mixture was cooled in an ice bath, KOtBu (51.6 g, 2 equiv.) was added portionwise, the ice bath was removed, and the mixture was stirred for 30 minutes at room temperature. Extraction with DCM/H2O, drying over Na2SO4 and evaporation under reduced pressure gave 40 grams of crude material, which was purified by flash chromatography eluting with DCM. This yielded 20.4 grams of an orange oil which solidified upon standing. 1H NMR (400 MHz, CDCl3) δ 1.29 (t, J=7.5 Hz, 6H), 2.00 (q, J=7.5 Hz, 4H).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred for 30 minutes at room temperature
  4. extractionExtraction with DCM/H2O
  5. dry with materialdrying over Na2SO4 and evaporation under reduced pressure

Sources & evidence

ORD record
ord-70c666ce7b4a4ede94971688eaf95325
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

Loading…