Reaction #11540

Reaction equation

hydrochloric acid

diethyl 2-methyl-2-(4-pyridylmethyl)malonate

→

2-methyl-3-(4-pyridyl)propionic acid

Yield 100.3%

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed overnight
2. 2
   Washwashed with hexane (100 ml)
3. 3
   Otherto remove sodium hydride oil
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   FiltrationThe resulting crystals were filtered off with ethyl acetate

Procedure

Next, 6 N hydrochloric acid (96.8 ml, 581 mmol) was added to diethyl 2-methyl-2-(4-pyridylmethyl)malonate (17.2 g, 64.6 mmol), and the mixture was refluxed overnight. The reaction mixture was allowed to stand, then washed with hexane (100 ml) to remove sodium hydride oil contained in diethyl 2-methyl-2-(4-pyridylmethyl)malonate, and concentrated under reduced pressure. The resulting crystals were filtered off with ethyl acetate to give 10.7 g (82%) of 2-methyl-3-(4-pyridyl)propionic acid as pale pink crystals.

Source