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Methanol → 1-Cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-ene

HRID 1153695
Notes
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Reaction equation

HRID 1153695 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 538447631-Cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-eneYield 37.8%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

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 (Example 2) in 50 ml of dioxan was added dropwise to a suspension of 3 g of 80% strength sodium hydride in 100 ml of dioxan. When the addition had ended, the mixture was warmed to 50° C. for 1 hour. After cooling, 10.9 g (0.1 mol) of ethyl bromide were added dropwise and the reaction mixture was heated under reflux overnight. After cooling, 10 ml of methanol were added and the mixture was concentrated in a rotary evaporator. The residue was taken up in methylene chloride and the methylene chloride mixture was washed with water. After drying the organic phase 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. additionWhen the addition
  2. temperatureAfter cooling
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureAfter cooling
  6. concentrationthe mixture was concentrated in a rotary evaporator
  7. washthe methylene chloride mixture was washed with water
  8. dry with materialAfter drying the organic phase over sodium sulphate, it
  9. filtrationwas filtered
  10. concentrationthe filtrate was concentrated
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-f1fb8e7b005f4e0282219d2fe391a5e0
Source dataset
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04486218

Reaction notes

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