Heptanol → HCID 178444041, compound

HRID 249211Notes

Reaction equation

HRID 249211 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[CH2:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[N:29][C:30](Cl)=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)[CH3:12]>C1(C)C=CC=CC=1.O>[CH2:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[N:29][C:30]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

6

Reactant 3

HCID 8129HeptanolHCID 24758Sodium hydrideHCID 178455735HCID 178455735, compound

Product 1

HCID 178444041HCID 178444041, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

A solution of n-heptanol (3.5 g) in toluene (50 ml) was dropwise added to a suspension of sodium hydride (about 55%) (1.5 g) in toluene (50 ml). The mixture was agitated for 30 minutes, dropwise adding a solution of 3-(4-(2-(trans-4-ethylcyclohexyl)ethyl)phenyl)-6-chloropyridazine (5 g) obtained above, in toluene (100 ml), heating the mixture under reflux for 3 hours. The reaction solution was poured in water. The resulting organic layer was washed with water until the organic layer became neutral. After drying it over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure and recrystallizing the residue from ethanol, the captioned 3-(4-(2-(trans-4-ethylcyclohexyl)ethyl)phenyl)-6-heptyloxypyridazine (3.7 g) was obtained. ##STR12##

Workup

  1. temperatureheating the mixture
  2. temperatureunder reflux for 3 hours
  3. washThe resulting organic layer was washed with water until the organic layer
  4. dry with materialAfter drying it over anhydrous magnesium sulfate
  5. distillationdistilling off the solvent under reduced pressure
  6. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-6b0db9bc305e4be180fb2f55055156f0
Source dataset
uspto-grants-1993_05
Patent number
US05213708

Reaction notes

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