Formaldehyde → 1-Diethylamino-4(S)-acetyloxy-2nonyne

Participants

Reaction Steps

A mixture of 3(S)-acetyloxy-1-octyne (58.5 g., 0.35 mole), diethylamine (28.5 g., 0.39 mole), paraformaldehyde (13.8 g., 0.46 mole), and p-dioxane (60 ml.) is heated on the steam bath for 17 hours, then cooled to room temperature and diluted with ether (250 ml.). The resulting solution is extracted with 5% hydrochloric acid (300 ml.) providing an aqueous extract (acidic) which is made basic with 10% sodium hydroxide solution and extracted with ether. The organic extract is dried over sodium sulfate and filtered. In vacuo evaporation of the filtrate leaves a residual oil which is distilled to provide the title compound (73.1 g., 89%), b.p. 103°-109° C./0.3 mm.; [α]D26 -80° (C 3.3, CHCl3).

Provenance & Evidence