Tetrahydrofuran → HCID 18918573, compound

Participants

Reaction Steps

To a stirred solution of the product of step (iv) (2.6 g) in tetrahydrofuran (100 ml) was added lithium aluminium hydride (1.2 g) and the resulting suspension stirred for 4 hours at ambient temperature. Excess reducing agent was destroyed by the sequential addition of ethyl acetate, water, and conc. HCl. The mixture was then basified and extracted sequentially with ethyl acetate and dichloromethane. The organic extracts were combined, dried (PS paper and MgSO4) and evaporated to yield 4-dimethylamino-3-(3-hydroxypropyl)pyridine as a pale yellow oil (2.2 g), essentially pure by Tlc NMR (d6DMSO): δ1.6-1.8 (2H,m); 2.65 (2H,t); 2.8 (6H,s); 3.5 (2H,t); 4.5 (1H,br.s); 6.7 (2H,d); 8.2 (2H,d); m/e 181 (M+H)+.

Provenance & Evidence