Acetic Acid → 1-(Pyridazin-3-yl)ethan-1-ol

HRID 1503429Notes

Reaction equation

HRID 1503429 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[CH3:13]C(O)=O.OO>C1COCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([OH:5])[CH3:13])[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 58197546N-methoxy-N-methylpyridazine-3-carboxamide

Product 1

HCID 151975111-(Pyridazin-3-yl)ethan-1-olYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of compound 2 (300 mg, 0.6 mmol) in THF (15 mL) was added AcOH (1 mL) and H2O2 (3 mL). The reaction mixture was stirred at 30° C. for 10 h. The mixture was quenched with saturated NaHCO3 (6 mL) and then balanced between EtOAc (2×20 mL) and water (10 mL). The organic layers were collected and concentrated in vacuo to give the residue, which was purified by preparative TLC (petroleum ether:ethyl acetate=1:1) to give compound 3 (70 mg, 35%) as a colorless oil.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 (6 mL)
  2. customThe organic layers were collected
  3. concentrationconcentrated in vacuo
  4. customto give the residue, which
  5. customwas purified by preparative TLC (petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-54193b004b7548258da793e121d1e478
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

Loading…