Water → 3-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridine

Participants

Reaction Steps

Cyclopent-3-en-yl[2-(methyloxy)pyridin-3-yl]methanone (Preparation 29, 10 g, 49.3 mmol), potassium hydroxide (85%, 16.8 g, 0.3 mol), and hydrazine (6.33 g, 198 mmol) in ethylene glycol (100 ml) were heated to 180° C. and stirred for 18 h. Water was added and the product was extracted with hexane:ethyl acetate (50:50). The combined organic extracts were washed with brine and concentrated in vacuo. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (10:90) to give a colourless oil (4.75 g, 51%).

Provenance & Evidence