Hydrochloric Acid → HCID 64993550, compound

HRID 1774571Notes

Reaction equation

HRID 1774571 reaction equation
C([C:4]1[N:5]=[CH:6][S:7][CH:8]=1)(=O)C.[CH3:9][O:10][CH:11]([O:16][CH3:17])[C:12]([O:14]C)=O.[CH3:18][O-:19].[Na+].[CH3:21]O.Cl>C(OCC)C.C(OCC)(=O)C.O>[CH3:17][O:16][CH:11]([O:10][CH3:9])[C:12](=[O:14])[CH2:21][C:18]([C:6]1[S:7][CH:8]=[CH:4][N:5]=1)=[O:19]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 33480311-(Thiazol-4-yl)ethanoneHCID 10942334Sodium Methoxide

Product 1

HCID 64993550HCID 64993550, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-acetylthiazole (1.0 g, 7.86 mmol) and methyl dimethoxyacetate (1.05 g, 7.86 mmol) in anhydrous diethyl ether (15 mL) was treated with sodium methoxide 4.37M in methanol (1.80 mL, 7.86 mmol) at 0° C. The resulting mixture was stirred at room temperature for 3 hours, and then diluted with ethyl acetate (10 mL). After cooling to 0° C., the reaction mixture was neutralized with 1N hydrochloric acid until pH 3 was reached. Water was added (6 mL) and layers were separated. The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo to provide 4,4-dimethoxy-1-(1,3-thiazol-2-yl)butane-1,3-dione (8a) (1.58 g, 6.89 mmol, 88%) which was used without further purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customwere separated
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6377240c0a0f41ee8c234cd5e52110bb
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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