Iodoethane → HCID 22125074, compound

HRID 1858325Notes

Reaction equation

HRID 1858325 reaction equation
C(=O)=O.C[C:5]([CH3:7])=O.[N+:8]([C:11]1[CH:12]=[C:13]([CH2:17][C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].I[CH2:21][CH3:22].CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[Cl-].[NH4+]>O1CCCC1>[CH2:21]([C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)([CH2:5][CH3:7])[C:18]#[N:19])[CH3:22]

Participants

8

Reactant 6

HCID 6340IodoethaneHCID 121253-NitrophenylacetonitrileHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 18522661Acetone cardiceHCID 23665647Potassium tert-butoxide

Product 1

HCID 22125074HCID 22125074, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry-ice/acetone cooled solution of 2 g (12 mmol) of 3-nitrophenylacetonitrile in 100 ml of tetrahydrofuran was treated with 4.4 g (26.5 mmol) of iodoethane, 3 g (27 mmol) of potassium tert-butoxide and 800 mg (3 mmol) of 18-crown-6. The mixture was stirred for 18 hours allowing the reaction temperature to steadily rise to ambient temperature. 100 ml of saturated aqueous ammonium chloride were added and the organic phase separated, dried over magnesium sulfate, filtered and evaporated. The product was purified by flash chromatography on silica gel using diethyl ether/hexane in a ratio of 3:7 as eluent. Product-containing fractions were evaporated to give 2.1 g (80%) of 2-ethyl-2-(3-nitro-phenyl)-butyronitrile as a pale brown oil. [Mass spectrum (ESI) MH+ =219].

Workup

  1. customto steadily rise to ambient temperature
  2. customthe organic phase separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was purified by flash chromatography on silica gel
  7. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-4d229da200c8424983fc4534b4a26c71
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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