Methyl acetoacetate → Methyl 3-(3-thienylethyl)aminocrotonate

HRID 868682Notes

Reaction equation

HRID 868682 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.[C:9]([O:15][CH3:16])(=[O:14])[CH2:10][C:11]([CH3:13])=O>C(OCC)C>[S:6]1[CH:7]=[CH:8][C:4]([CH2:3][CH2:2][NH:1]/[C:11](/[CH3:13])=[CH:10]\[C:9]([O:15][CH3:16])=[O:14])=[CH:5]1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 122587372-(3-Thienyl)ethanamine

Product 1

HCID 21283660Methyl 3-(3-thienylethyl)aminocrotonateYield 97.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.8 grams (30 millimoles) of 3-(2-aminoethyl)thiophene was added dropwise with stirring at room temperature to 3.6 grams (31 millimoles) of methyl acetoacetate and the stirring was continued over the weekend at ambient temperature. Thereafter, the mixture was diluted with 250 milliliters of diethyl ether and the resulting ether solution washed with 50 milliliters of brine and then dried over sodium sulfate. The ether solvent was then vaporized from the dried and filtered solution to obtain 6.59 grams of a methyl 3-[(3-thienyl)ethyl]aminocrotonate intermediate as a slightly yellowish oil.

Workup

  1. customwas continued over the weekend at ambient temperature
  2. washthe resulting ether solution washed with 50 milliliters of brine
  3. dry with materialdried over sodium sulfate
  4. customdried
  5. filtrationfiltered solution

Sources & evidence

ORD record
ord-4686997e6c6b4a52b3007df2e06e64c1
Source dataset
uspto-grants-1988_10
Patent number
US04780538

Reaction notes

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