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

HRID 1165697Notes

Reaction equation

HRID 1165697 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(prepared as described in Example II-1) were taken up in 200 methanol, and 4.5 g of sodium borohydride were added in portions to the solution, while stirring and cooling. After the reaction had ended, the reaction mixture was adjusted to pH 6 and was concentrated. The residue was taken up in 200 ml of methylene chloride, and the solution was washed with saturated sodium bicarbonate solution, dried over sodium sulphate, filtered and concentrated. The residue was recrystallized 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. additionwere added in portions to the solution
  2. temperaturecooling
  3. concentrationwas concentrated
  4. washthe solution was washed with saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-6aa6bb66ae824274ad324ceaff3daa86
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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