Methanol → HCID 53844763, compound

HRID 1905587Notes

Reaction equation

HRID 1905587 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 (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-eea55844426c4b2684e4a23e0f29336c
Source dataset
uspto-grants-1987_03
Patent number
US04647302

Reaction notes

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