Ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)acrylate → Ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)propanoate

HRID 709755Notes

Reaction equation

HRID 709755 reaction equation
[CH:1]1([C:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1>C(O)(=O)C.[Zn]>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 131733914Ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)acrylate

Product 1

HCID 117759691Ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-3-(2-methoxypyridin-4-yl)acrylate in acetic acid (100 mL) was added a zinc powder (16.3 g), and the mixture was stirred at room temperature for 5 min. The reaction mixture was filtered, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (4.17 g) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3eb5cfb8ca284b6f8ab8215e611ec6eb
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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