Sodium borohydride → alpha-Zearalenol

HRID 972217Notes

Reaction equation

HRID 972217 reaction equation
[BH4-].[Na+].[CH3:3][C@@H:4]1[O:23][C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([OH:25])=[CH:18][C:19]=2[OH:24])[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5]1>CO>[CH3:3][C@@H:4]1[O:23][C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([OH:25])=[CH:18][C:19]=2[OH:24])[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][C@@H:8]([OH:9])[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12445020cis-Zearalenone

Product 1

HCID 5284645alpha-Zearalenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1 gram) is slowly added to 50 milliliters of methanol and 0.3 gram of cis-zearalenone while cooling the resultant reaction mixture. The mixture is then heated for 2 hours on a steam bath to evaporate the methanol. The residue is neutralized with HCl and extracted with two 40 milliliter portions of chloroform. The chloroform is then evaporated and the residue is purified by the column chromatography procedure of Example III, above, to yield about 0.28 gram of mixed diamers of cis-zearalenol.

Workup

  1. temperaturewhile cooling the resultant
  2. customreaction mixture
  3. temperatureThe mixture is then heated for 2 hours on a steam bath
  4. customto evaporate the methanol
  5. extractionextracted with two 40 milliliter portions of chloroform
  6. customThe chloroform is then evaporated
  7. customthe residue is purified by the column chromatography procedure of Example III

Sources & evidence

ORD record
ord-c87c2e14724f44269c35b7da9fec5e00
Source dataset
uspto-grants-1977_10
Patent number
US04052414

Reaction notes

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