Ethyl Acrylate → Ethyl 4-cyano-5-methyl-4-(3-thienyl)hexanoate

HRID 1071635Notes

Reaction equation

HRID 1071635 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#[N:8])=[CH:2]1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11].[CH3:16][C:17](C)([O-])[CH3:18].[K+]>CN(C)C=O>[C:7]([C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([CH:17]([CH3:18])[CH3:16])[CH2:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])#[N:8]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 837303-ThienylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 22393748Ethyl 4-cyano-5-methyl-4-(3-thienyl)hexanoateYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Methyl-2-(3-thienyl)butanenitrile (6.23 g) obtained using 3-thienylacetonitrile as a starting material in accordance with the method of Example 114 described in JP-A 11-206862 and ethyl acrylate (4.53 g) were dissolved in dimethylformamide (15 ml), and added at a room temperature to a solution of potassium tert-butoxide (423 mg) in dimethylformamide solution (60 ml). After stirring 5 hours as it was, the organic layer was separated by adding an aqueous saturated ammonium chloride and diethyl ether thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a yellow oil (6.66 g, 67%).

Workup

  1. customthe organic layer was separated
  2. additionby adding an aqueous saturated ammonium chloride and diethyl ether
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-4496b3a7511f42b38650807819523dad
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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