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

HRID 572119Notes

Reaction equation

HRID 572119 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 to give a crude solid. This was washed with hexane to give 2-[(hydroxy)(pyridin-3-yl)methyl]acrylic acid ethyl ester (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, 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. customto give a crude solid
  3. washThis was washed with hexane

Sources & evidence

ORD record
ord-ee334a3060d44952b228f6bbed16ae94
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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