Ethyl Acrylate → Ethyl-2-(hydroxy(pyridin-3-yl)methyl)acrylate

HRID 572138Notes

Reaction equation

HRID 572138 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11]>C1N2CCN(CC2)C1>[CH2:14]([O:13][C:9](=[O:12])[C:10]([CH:1]([OH:8])[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH2:11])[CH3:15]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 15812391Ethyl-2-(hydroxy(pyridin-3-yl)methyl)acrylateYield 95.6%

Reagents, catalysts & solvents 1

HCID 9237DabcoCatalyst

Procedure

To a solution of nicotinaldehyde (10.0 g, 93.4 mmol) in ethyl acrylate (20 mL, ˜200 mmol) at room temperature was added DABCO (0.5 g, 4.5 mmol) and the mixture was stirred overnight. Excess ethyl acrylate was removed in vacuo. The resulting crude solid was washed with hexane to give the title compound (18.5 g, 95%) as an off-white solid. δH (CDCl3) 8.62 (d, J 1.7 Hz, 1H), 8.53 (dd, J 4.8, 1.3 Hz, 1H), 7.81 (d, J 7.9 Hz, 1H), 7.28 (s, 1H), 6.42 (s, 1H), 5.93 (s, 1H), 5.63 (s, 1H), 4.18 (m, 2H), 3.20 (br s, 1H), 1.27 (t, J 7.1 Hz, 3H). LCMS (ES+) 208.2 (M+H)+.

Workup

  1. customExcess ethyl acrylate was removed in vacuo
  2. washThe resulting crude solid was washed with hexane

Sources & evidence

ORD record
ord-cd752341962c4a7bbe0f617b270499a5
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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