Hydrochloric Acid → HCID 62745196, compound

HRID 1774578Notes

Reaction equation

HRID 1774578 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[CH3:10][O:11][CH:12]([O:17][CH3:18])[C:13](OC)=[O:14].C[O-].[Na+].CO.Cl>C(OCC)C.C(OCC)(=O)C.O>[CH3:10][O:11][CH:12]([O:17][CH3:18])[C:13](=[O:14])[CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 142862-AcetylpyridineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 62745196HCID 62745196, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-acetylpyridine (3.0 g, 24.8 mmol) and methyl dimethoxyacetate (3.32 g, 24.8 mmol) in anhydrous diethyl ether (45 mL) was treated with sodium methoxide 4.37M in methanol (5.67 mL, 24.8 mmol) at 0° C. The resulting mixture was stirred at room temperature for 3 days, and then diluted with ethyl acetate (10 mL). After cooling to 0° C., the reaction mixture was neutralized with 1N hydrochloric acid until pH 6-7 was reached. Water was added (10 mL) and the layers were separated. The organic layer was washed with brine (25 mL), dried over sodium sulfate and concentrated in vacuo to provide 4,4-dimethoxy-1-(pyridin-2-yl)butane-1,3-dione (9a) (5.11 g, 22.9 mmol, 92%) which was used without further purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe layers were separated
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b344424a0f0147da9584f60d49a5e8d8
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

Loading…