Ethyl Acrylate → HCID 66693519, compound

HRID 572134Notes

Reaction equation

HRID 572134 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20]>>[CH2:23]([O:22][C:18](=[O:21])[C:19]([CH:8]([OH:9])[C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[CH2:20])[CH3:24]

Participants

4

Reactant 3

HCID 8821Ethyl AcrylateHCID 9237DabcoHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 66693519HCID 66693519, compoundYield 62%

Procedure

To a solution of 6-methylpyridine-3-carbaldehyde (5.0 g, 41 mmol) in ethyl acrylate (10 mL) at room temperature was added DABCO (1.0 g, 9 mmol), and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (SiO2, hexane to 40% ethyl acetate), to give the title compound (5.6 g, 62%) as a yellow oil. LCMS (ES+) 222.2 (M+H)+, RT 0.98 minutes.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography (SiO2, hexane to 40% ethyl acetate)

Sources & evidence

ORD record
ord-dfd1e396b2564d8a8487e8be58b6e026
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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