Acetic Acid → Sodium triacetoxyborohydride

HRID 647391Notes

Reaction equation

HRID 647391 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 suspension of sodium borohydride (69.8 mg.) in benzene (15 ml.) is treated with acetic acid (92 mg.) and refluxed for 1 hour under nitrogen to afford a clear solution of sodium triacetoxyborohydride. To this solution is added a solution of 2S,3R,6R-6-(2-oxoethyl)-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxidooxepane (158 mg.) in benzene (5 ml.) and the mixture refluxed for 5 hours under nitrogen. The solvent is removed in vacuo, the residue diluted with water and extracted with methylene chloride. Removal of the solvent from the dried organic phase affords a residue which is plate chromatographed on silica gel, using ethyl acetate:chloroform (4:1) as the developing solvent. The major band is eluted with ethyl acetate to afford 2S,3R-6-(2-hydroxyethyl)-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxidooxepane (121 mg.):

Workup

  1. temperaturerefluxed for 1 hour under nitrogen

Sources & evidence

ORD record
ord-fb3d61c335d54fe2872e1465606fe32a
Source dataset
uspto-grants-1983_10
Patent number
US04408060

Reaction notes

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