Ethyl Acrylate → HCID 22718311, compound

HRID 1582770Notes

Reaction equation

HRID 1582770 reaction equation
[CH3:1][CH:2]([CH3:11])[CH:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]#[N:5].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.CCCCCC>[C:4]([C:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)([CH:2]([CH3:11])[CH3:1])[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])#[N:5]

Participants

8

Reactant 4

HCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 123819863-Methyl-2-(2-thienyl)butanenitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 22718311HCID 22718311, compoundYield 62.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Methyl-2-(2-thienyl)butane nitrile 5.56 g 33.6 mmol and ethyl acrylate 4.00 ml 37.0 mmol were dissolved in tetrahydrofuran 100 ml. Potassium t-butoxide, 566 mg 5.04 mmol, was added little by little thereto at room temperature. Generation of heat continued during this step. After stirring for 1 hour, brine 100 ml and aqueous saturated ammonium chloride 150 ml were added thereto successively, and the mixture was extracted with ether 1 L. The organic layer was washed with brine 500 ml and water 500 ml successively, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound (5.57 g 21.0 mmol, 62.5%) was obtained as a yellow oil.

Workup

  1. temperatureGeneration of heat
  2. extractionsuccessively, and the mixture was extracted with ether 1 L
  3. washThe organic layer was washed with brine 500 ml and water 500 ml successively
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated

Sources & evidence

ORD record
ord-159b52f2ae32472d8d838766c1bbfc70
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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