Hydrochloric Acid → HCID 53907172, compound

HRID 568316Notes

Reaction equation

HRID 568316 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:23])([CH3:22])[C:10](=[O:21])[C:11]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:22])([CH3:23])[CH:10]([OH:21])[C:11]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54324090HCID 54324090, compound

Product 1

HCID 53907172HCID 53907172, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

7 g (0.021 mol) of 1-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-octen-3-one (Example 1) are dissolved in 100 ml of methanol, and a solution of 0.21 g (0.006 mol) of sodium borohydride in 5 ml of icewater is added dropwise at -10° C. The reaction mixture is subsequently stirred at 0° C. for 1.5 hours and is then adjusted to a pH value of 6 to 7 with dilute hydrochloric acid. The reaction mixture is concentrated by distilling off the solvent in vacuo. The residue is taken up in chloroform and the mixture is washed with water, dried over sodium sulphate and concentrated. 6.5 g (92.9% of theory) of 1-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-octen-3-ol of refractive index nD20 1.5383 are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. distillationby distilling off the solvent in vacuo
  3. washthe mixture is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ee10c9e2250402f8f8c72b7e62feb6c
Source dataset
uspto-grants-1988_03
Patent number
US04728356

Reaction notes

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