Ethyl Acetate → Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanate

HRID 1071624Notes

Reaction equation

HRID 1071624 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:9]1[CH:13]=[C:12]([CH:14]([C:18]#[N:19])[CH:15]([CH3:17])[CH3:16])[S:11][CH:10]=1)#[N:8].[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>CN(C=O)C>[C:18]([C:14]([C:12]1[S:11][CH:10]=[C:9]([C:7]#[N:8])[CH:13]=1)([CH:15]([CH3:16])[CH3:17])[CH2:1][CH2:21][C:20]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 223936703-Cyano-5-(1-cyano-2-methylpropyl]thiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22393597Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium tert-butoxide (35 mg) was suspended in DMF (5 ml), and a DMF solution (5 ml) of 3-cyano-5-(1-cyano-2-methylpropyl]thiophene (0.60 g) was added thereto. After stirring at room temperature for 3.5 hours, ethyl acetate was added. The mixture was washed with an aqueous saturated ammonium chloride and further brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound as a pale yellow oil (0.55 g, 60%).

Workup

  1. washThe mixture was washed with an aqueous saturated ammonium chloride and further brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-ea03a3065fc448d0a202be055f38092d
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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