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Naamsigna Dave

Role of methanol in NaBH4 reduction

Bob Collier  Follow

I believe methanol does protonate the alkoxide. The resulting methoxide coordinates to $\ce{BH3}$ forming $\ce{(MeO)BH3-}.$ The electron donating character of the methoxy group makes the remaining protons more hydride which results in a more reactive hydride source.

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Fashion and Style  Follow
, 3, 1431–1440More
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John Barton  Follow
This is probably the reference in question: More
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Jackie Howe Janssen  Follow
Interesting, but a reference maybe?More
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Fran?oise Marie  Follow
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, More
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GMR- The Marketing Guy  Follow
J. Org. Chem.More
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Carlo Bergonzoni  Follow

You need methanol to solve NaBH4, other solvents are not very suitable. The active reducing species can be NaBH4 or NaOCHxHx (in which NaBH4 has first reacted with methanol)

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