Methanol → HCID 53844763, compound

HRID 1165698Notes

Reaction equation

HRID 1165698 reaction equation
[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])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:22](Br)[CH3:23].CO>O1CCOCC1>[CH:1]1([CH:7]=[C:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:9]([O:14][CH2:22][CH3:23])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 1148141-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol

Product 1

HCID 53844763HCID 53844763, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 26.3 g (0.1 mol) of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol (prepared as described in Example II-2) in 50 ml of dioxane was added dropwise to a suspension of 3 g of 80% strength sodium hydride in 100 ml of dioxane. After the addition had ended, the mixture was warmed to 50° C. for 1 hour. After the mixture had cooled, 10.9 g (0.1 mol) of ethyl bromide were added dropwise to it, and the reaction mixture was heated under reflux overnight. After the mixture had cooled, 10 ml of methanol were added to it and it was concentrated in a rotary evaporator. The residue was taken up in methylene chloride and was washed with water. After the organic phase had been dried over sodium sulphate, it was filtered and the filtrate was concentrated. The residue was distilled. 11.0 g (37.8% of theory) of 1-cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent- 1-ene of boiling point 110° C./0.07 mm Hg were obtained.

Workup

  1. additionAfter the addition
  2. temperatureAfter the mixture had cooled
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureAfter the mixture had cooled
  6. concentrationwas concentrated in a rotary evaporator
  7. washwas washed with water
  8. dry with materialAfter the organic phase had been dried over sodium sulphate, it
  9. filtrationwas filtered
  10. concentrationthe filtrate was concentrated
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-289b24118523431d8e79f24712f4c4db
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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