Iodine → HCID 19789782, compound

HRID 1655938Notes

Reaction equation

HRID 1655938 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[Cl:5][C:6]1([C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH2:8][CH2:7]1.II>O1CCCC1.[Zn]>[Cl:5][C:6]1([C:9]([OH:16])([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH2:3][CH:2]=[CH2:1])[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 807IodineHCID 7841Allyl bromideHCID 143483801-(1-Chlorocyclopropyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 19789782HCID 19789782, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 12. 1 g (0.1 mol) of allyl bromide and 16.65 g (0.09 mol) of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 50 ml of tetrahydrofuran are added dropwise at 20° C. under nitrogen atmosphere in the course of 0.5 hours to a stirred mixture of 7.2 g (0.11 mol) of zinc dust, 0.1 g of iodine and 50 ml of absolute tetrahydrofuran. When the addition has ended, stirring is continued for 24 hours at room temperature, the mixture is then concentrated by stripping off the solvent and treated with aqueous ammonium chloride solution. The resulting mixture is extracted several times using dichloromethane. The combined organic phases are dried over sodium sulphate and then concentrated by stripping off the solvent under reduced pressure. In this manner, 10.2 g (50% of theory) of (4-(1-chloro-cyclopropyl)-4-hydroxy-5-(1,2,4-triazol1-yl)-pent-1-ene are obtained in the form of a solid substance of melting point 75° to 76° C. ##STR40##

Workup

  1. additionWhen the addition
  2. concentrationthe mixture is then concentrated
  3. additiontreated with aqueous ammonium chloride solution
  4. extractionThe resulting mixture is extracted several times
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ecdc55feb314ae58abfc300035deed0
Source dataset
uspto-grants-1993_10
Patent number
US05252582

Reaction notes

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