I want to synthesize 3-hydroxydihydrofuran-2-one from formaldehyde but I do not know of a method. I tried a Mannich reaction and lactonization after dehydration.


Starting from pyruvic acid which is readily available and not very expensive: react pyruvic acid (only one enolizable side) with a Mannich base, then react the resulting amide with $\ce{MeI}$ and base to obtain the exo-methylene product. Brominate the exo-methylene. Now cyclization will prefer the five-membered ring over the strained four-membered ring. Reduce the ketone with a reletively mild reducing agent like $\ce{NaBH4}$ and then eliminate $\ce{HBr}$ in a E1cB type reaction, yielding 3-hydroxydihydrofuran-2-one.

This synthesis involves a Mannich reaction as you asked, but it can be done much simpler without it I think.

Note: I'm not an expert, just an enthusiastic amateur. Before trying anything in the lab make sure your synthesis is checked by a supervisor.

  • $\begingroup$ Thank you so much! Your explanation is very clear. Fortunately, I don't make anything in laboratory, just I write this synthesis in my homework, but thanks for the prompt. $\endgroup$ – Paola Stornello Feb 9 '15 at 14:06
  • $\begingroup$ Jori, can you show me the other method without the Mannich reaction? Thanks a lot for the help $\endgroup$ – Paola Stornello Feb 9 '15 at 20:42

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