Water → 4-[(6-Chloro-3-pyridazinyl)oxy]benzenemethanol

HRID 347676Notes

Reaction equation

HRID 347676 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 17859705HCID 17859705, compound

Product 1

HCID 178597134-[(6-Chloro-3-pyridazinyl)oxy]benzenemethanolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-Chloro-6-(4-formylphenoxy)pyridazine (4.06 g, 17.3 mmol) and 200 mL of methanol were mixed, and after sodium borohydride (654 mg, 17.3 mmol) was added under cooling with ice and stirring, the mixture was stirred for 15 minutes. Water was added to the reaction mixture and methanol was distilled off. The residue was poured into water, which was extracted with ethyl acetate. The extracted solution was washed with saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v) to obtain 3.10 g (76%) of the title compound as a colorless oily product.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 15 minutes
  3. distillationwas distilled off
  4. additionThe residue was poured into water, which
  5. extractionwas extracted with ethyl acetate
  6. washThe extracted solution was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v)

Sources & evidence

ORD record
ord-dadae83fcd9645f797ee40cdeb618f20
Source dataset
uspto-grants-2007_02
Patent number
US07176204B2

Reaction notes

Loading…