Sodium hydride → HCID 22913364, compound

HRID 1377377Notes

Reaction equation

HRID 1377377 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH:10]([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12].[CH2:17]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[N:34][C:35](Cl)=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1(C)C=CC=CC=1>[CH2:17]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:33]=[N:34][C:35]([O:12][CH2:11][CH:10]([O:9][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][O:3]3)[C:13]([F:14])([F:15])[F:16])=[CH:36][CH:37]=2)=[CH:30][CH:31]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13650965HCID 13650965, compoundHCID 22913409HCID 22913409, compound

Product 1

HCID 22913364HCID 22913364, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A mixture of sodium hydride (100 mg) with toluene (10 ml) was stirred under ice cooling, followed by gradually dropwise dropping a mixed solution of optically active 2-(2-tetrahydropyranyloxy)-3,3,3-trifluoro-1-propanol obtained in Example 3 (450 mg) with toluene (4 ml), stirring the mixture at room temperature for one hour, pouring a solution of 3-(4-nonylphenyl)-6-chloropyridazine (540 mg) in toluene (10 ml) in the mixture, stirring at 80° C. for 2 hours, extracting the reaction mixture with toluene, washing till the washing liquid became neutral, removing the solvent, purifying according to silica gel chromatography, and drying the residue by a vacuum pump, to obtain 3-(4-nonylphenyl)-6-(2-(2-tetrahydropyranyloxy)-3,3,3-trifluoropropoxy)pyridazine. Yield: 700 mg. m.p. 96.1° C.

Workup

  1. stirringstirring the mixture at room temperature for one hour
  2. stirringstirring at 80° C. for 2 hours
  3. extractionextracting the reaction mixture with toluene
  4. washwashing till the washing liquid
  5. customremoving the solvent
  6. custompurifying
  7. customdrying the residue by a vacuum pump

Sources & evidence

ORD record
ord-87347101f95c4360ab63d3fe077f2056
Source dataset
uspto-grants-1997_09
Patent number
US05665270

Reaction notes

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