Acetic Acid → Sodium triacetoxyborohydride

HRID 126687Notes

Reaction equation

HRID 126687 reaction equation
[BH4-:1].[Na+:2].[C:3]([OH:6])(=[O:5])[CH3:4]>C1C=CC=CC=1>[C:3]([O:6][BH-:1]([O:6][C:3](=[O:5])[CH3:4])[O:5][C:3](=[O:6])[CH3:4])(=[O:5])[CH3:4].[Na+:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 4311764Sodium borohydride

Product 1

HCID 5049666Sodium triacetoxyborohydride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene suspension of 8 equivalents of sodium borohydride was refluxed with 6.5 equiv. of glacial acetic acid for 15 minutes under a nitrogen atmosphere to give a clear solution of sodium triacetoxyborohydride. To this solution was added a benzene solution of 510 mg; 1 mmol of compound (III-a) and the mixture was refluxed for 1 hour. The reaction mixture was then diluted with water and extracted with chloroform. The further work-up and column chromatographic purification described in Example 4 were carried out, to give the title compound as characterized in Example 4. The yield according to this procedure was higher than in Example 4.

Sources & evidence

ORD record
ord-cf68285c012e468bb03f299b0b3d11cd
Source dataset
uspto-grants-1981_03
Patent number
US04254110

Reaction notes

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