Sodium borohydride → Triapenthenol

HRID 1981457Notes

Reaction equation

HRID 1981457 reaction equation
[CH:1]1(/[CH:7]=[C:8](/[N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)\[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1(/[CH:7]=[C:8](/[N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)\[CH:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12763477(E)-1-cyclohexyl-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one

Product 1

HCID 6437842TriapenthenolYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

26 g (0.1 mol) of (E)-1-cyclohexyl-4,4-dimethy-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one are taken up in 200 ml of methanol, and 4.5 g of sodium borohydride are added in portions, while stirring and cooling. When the reaction has ended, the reaction mixture is brought to pH 6 and concentrated. The residue is taken up 200 ml of methylene chloride, the mixture is washed with saturated sodium bicarbonate solution, dried over sodium sulphate and filtered and the filtrate is concentrated. The residue is recrystallised from petroleum ether. 14.5 g (55% of theory) of racemic (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene of melting point 131° C. are obtained.

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. washthe mixture is washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. customThe residue is recrystallised from petroleum ether

Sources & evidence

ORD record
ord-63aca424864648d3b63fb5255bd29527
Source dataset
uspto-grants-1986_06
Patent number
US04592772

Reaction notes

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