Methanol → Dimethyl 2-(2-(pyridin-4-yl)ethyl)malonate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of elemental sodium (20 g, 840 mmol) and CH3OH (600 ml) was added dimethyl malonate 10-1 (135 ml, 1120 mmol). After 5 minutes, 4-vinyl pyridine 10-2 (15.3 ml, 140 mmoles) was added and the solution was heated to 50° C. for 18 h. The reaction was diluted with EtOAc and then washed with sat NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatoraphy (silica, 60% EtOAc/hexanes) furnished the diether 10-3 (19.1 g) as a yellow oil.

Provenance & Evidence