Sodium borohydride → 1-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol

HRID 1905586Notes

Reaction equation

HRID 1905586 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 566097071-Cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one

Product 1

HCID 1148141-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-olYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-646d341669584e78b4f5a89f1221eac2
Source dataset
uspto-grants-1987_03
Patent number
US04647302

Reaction notes

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