Prasanth, C. P.; Joseph, Ebbin; Abhijith, A.; Nair, D. S.; Ibnusaud, Ibrahim; Raskatov, Jevgenij; Singaram, Bakthan published the artcile< Stabilization of NaBH4 in Methanol Using a Catalytic Amount of NaOMe. Reduction of Esters and Lactones at Room Temperature without Solvent-Induced Loss of Hydride>, COA of Formula: C6H10O5, the main research area is sodium borohydride methanol catalysis reduction ester lactone.
Rapid reaction of NaBH4 with MeOH precludes its use as a solvent for large-scale ester reductions We have now learned that a catalytic amount of NaOMe (5 mol %) stabilizes NaBH4 solutions in methanol at 25 °C and permits the use of these solutions for the reduction of esters to alcs. The generality of this reduction method was demonstrated using 22 esters including esters of naturally occurring chiral γ-butyrolactone containing dicarboxylic acids. This method permits the chemoselective reductions of esters in the presence of cyano and nitro groups and the reductive cyclization of a pyrrolidinedione ester to a fused five-membered furo[2,3-b]pyrrole and a (-)-crispine A analog in high optical and chem. yields. Lactones, aliphatic esters, aromatic esters containing electron-withdrawing groups, and heteroaryl esters are reduced more rapidly than aryl esters containing electron-donating groups. The 11B NMR spectrum of the NaOMe-stabilized NaBH4 solutions showed a minor quartet due to monomethoxyborohydride (NaBH3OMe) that persisted up to 18 h at 25 °C. We postulate that NaBH3OMe is probably the active reducing agent. In support of this hypothesis, the activation barrier for hydride transfer from BH3(OMe)- onto benzoic acid Me ester was calculated as 18.3 kcal/mol.
Journal of Organic Chemistry published new progress about Aliphatic esters Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics