Ethanol → HCID 21329198, compound

HRID 2420452Notes

Reaction equation

HRID 2420452 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[N:9][C:8]([C:11]([O:13]C)=O)=[CH:7][CH:6]=1.C(O)C.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:19][CH3:20]>>[CH3:3][O:4][C:5]1[N:10]=[N:9][C:8]([C:11](=[O:13])[CH:19]([CH3:20])[C:18]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 7749Ethyl PropionateHCID 24758Sodium hydrideHCID 21817223HCID 21817223, compound

Product 1

HCID 21329198HCID 21329198, compoundYield 52.5%

Procedure

Ethyl 3-(6-methoxypyridazin-3-yl)-2-methyl-3-oxopropionate is prepared by the fractional addition, over a period of 20 minutes, of sodium hydride (19.2 g) (50% in mineral oil) to a solution of methyl 6-methoxypyridazine-3-carboxylate (50 g) in ethyl propionate (220 g) at a temperature of about 98° C. The reaction mixture is maintained under reflux for a further 30 minutes. It is subsequently cooled to a temperature of about 20° C, and ethanol (10 cc) is added with care, followed by distilled water (800 cc). The aqueous phase is removed, washed by decantation with diisopropyl ether (3 × 250 cc), pure acetic acid (250 cc) is added (pH = 5-6) and the aqueous phase is washed again with ethyl acetate (3 × 150 cc). The organic phases are combined, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (30 mm Hg) to give ethyl 3-(6-methoxypyridazin-3-yl)-2-methyl-3-oxopropionate (37.2 g) in the form of a yellow oil.

Workup

  1. temperatureThe reaction mixture is maintained
  2. temperatureunder reflux for a further 30 minutes
  3. additionis added with care
  4. distillationby distilled water (800 cc)
  5. customThe aqueous phase is removed
  6. washwashed by decantation with diisopropyl ether (3 × 250 cc), pure acetic acid (250 cc)
  7. additionis added (pH = 5-6)
  8. washthe aqueous phase is washed again with ethyl acetate (3 × 150 cc)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness under reduced pressure (30 mm Hg)

Sources & evidence

ORD record
ord-641e362f24434b2d94e524a1d5a30e7d
Source dataset
uspto-grants-1978_08
Patent number
US04110450

Reaction notes

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