4-Pyridinecarboxaldehyde (98%, Acros Organics)
Methyl acrylate (99%, stabilized with MEHQ, TCI America)
1,4-Diazabicyclo[2.2.2]octane (DABCO, 98%, TCI America)
Dichloromethane (99.5%, stabilized with amylene, Alfa Aesar)

4-pyridinecarboxaldehyde (0.38 mL, 4.0 mmol), then methyl acrylate (0.48 mL, 5.2 mmol), were both added to a 2 dram (7.5 mL) reaction vial. The mixture was stirred rapidly with a magnetic stir bar prior to adding 1,4-Diazabicyclo[2.2.2]octane (45 mg, 0.40 mmol). The reaction mixture was stirred at 23 °C for 45 min; at which time, 4 mL of dichloromethane was added, prior to breaking up the solid with a metal spatula. The solid was collected via vacuum filtration using a hirsch filter. Recrystallization from a minimum amount of ethanol provided methyl 2-(hydroxy(pyridin-4-yl)methyl)acrylate (0.60 g, 3.1 mmol, 78% yield).

Methyl acrylate is extremely volatile and very toxic. This reaction was carried out in a fume hood.

¹H NMR (400 MHz, CDCl₃): δ 8.56 (d, 2H), 7.32 (d, 2H), 6.39 (s, 1H), 5.87 (s, 1H), 5.52 (s, 1H), 3.75 (s, 3H).
¹³C NMR (100 MHz, CDCl₃): δ 166.62, 150.38, 149.84, 140.75, 127.39, 121.31, 72.42, 52.20.
M.p. 142-143°C (lit. 143–144 ºC)

R.D. Crouch and T.D. Nelson, J. Chem. Ed. 1995, 72 (1), A6. DOI: 10.1021/ed072pA6

Y. Jeong and J.S. Ryu, J. Org. Chem. 2010, 75 (12), 4183. DOI: 10.1021/jo100618d