Water → HCID 56988340, compound

HRID 465284Notes

Reaction equation

HRID 465284 reaction equation
[CH2:1]([O:4][C@@H:5]([CH3:11])[CH2:6][CH2:7][C@@H:8]([OH:10])[CH3:9])[CH2:2][CH3:3].[Na].Cl[C:14]1[N:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1.O>C1(C)C=CC=CC=1>[CH3:9][C@H:8]([O:10][C:14]1[N:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)[CH2:7][CH2:6][C@@H:5]([O:4][CH2:1][CH2:2][CH3:3])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 197001373-Chloro-6-[4-(octyloxy)phenyl]pyridazineHCID 57234618HCID 57234618, compound

Product 1

HCID 56988340HCID 56988340, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

320 mg (2.0 mM) of the (2S,5S)-5-propoxy-2-hexanol obtained in Reference Example 1 was dissolved in 15 ml of anhydrous toluene. Thereto was added metallic sodium with stirring at room temperature. To the mixture was added 478 g (1.5 mM) of 3-chloro-6-(4-octyloxyphenyl)pyridazine. The resulting mixture was refluxed for 3 hours. The reaction mixture was cooled and mixed with water and toluene. The toluene layer was separated and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography [eluting solvent: n-hexane-ethyl acetate (4:1)] to obtain 190 mg of the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe toluene layer was separated
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was subjected to silica gel column chromatography [eluting solvent: n-hexane-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-472b7d829f754ab68c0b4960988ab6dc
Source dataset
uspto-grants-1992_10
Patent number
US05152919

Reaction notes

Loading…