Sodium borohydride → HCID 54216095, compound

HRID 1165702Notes

Reaction equation

HRID 1165702 reaction equation
[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[C:4](=[O:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)(C)C>[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[CH:4]([OH:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53942418HCID 53942418, compound

Product 1

HCID 54216095HCID 54216095, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

162 g (0.5 mol) of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-one (prepared as described in Example III-2) were dissolved in 500 ml of isopropanol, and 9.5 g (0.25 mol) of sodium borohydride were added in portions to the solution, while stirring. The reaction mixture was stirred for 10 hours at room temperature, and was then concentrated in vacuo. The residue was taken up in toluene, and the solution was washed with dilute acetic acid and then with water, and was dried over sodium sulphate and concentrated in vacuo. 156.6 g (96% of theory) of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-ol of refractive index nD20 =1.5579 were obtained as an E/Z isomer mixture.

Workup

  1. stirringThe reaction mixture was stirred for 10 hours at room temperature
  2. concentrationwas then concentrated in vacuo
  3. washthe solution was washed with dilute acetic acid
  4. dry with materialwith water, and was dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a91398c5a7849f6b36e67a90df8c924
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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