Dear Community,
I have a molecule with an aldehyd group that I want to reduce to the alcohol. The molecule also has two esther groups. When I react the molecule with NaBH4 (1 eq.) under soft conditions (room temperature, 3h) no reduction is taking place, under harsh conditions (heat, over night) also the esther groups are reduced. [Solvent THF in both cases]
Does anyone have a recommendation for suitable reaction conditions for NaBH4 reduction? Or experience with NaBH4 reductions?
Best regards,
Christian
It may be beneficial to add a little MeOH or EtOH to aid solubility if the ester groups are not subject to alcohol exchange. There is a large amount of literature on NaBH4 reductions and it would seem that discussion of a similar problem can be found there.
Christian Schnurr There is evidence of ester reduction in systems using NaBH₄-MeOH and THF, as reported in this study: Jorge C. S. da Costa et al., Arkivoc, 2006, 1, pp. 128-133. DOI:10.3998/ark.5550190.0007.115. In my undergraduate thesis (2021), I worked on the reductive amination of an aldehyde using 2.0 equivalents of NaBH₄ in an acidic medium (with 10 equivalents of acetic acid (AcOH)), but in an ice bath (0 ºC). You could try optimizing the reaction conditions. Additional conditions are also discussed in this work: Periasamy, M., Thirumalaikumar, M., 2000. J. Organomet. Chem. 609, 1-2, 137-151.
- Badges
- Science topic
- Similar topics
- Engineering
- Materials Engineering
- Powders