Potassium Carbonate → HCID 53840462, compound

HRID 463423Notes

Reaction equation

HRID 463423 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][N:9]=[C:10]([C:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[CH3:16])[C:11]([O:13][CH3:14])=[O:12].S(Cl)([Cl:26])(=O)=O>C(Cl)(Cl)Cl>[CH3:7][O:8][N:9]=[C:10]([C:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[CH2:16][Cl:26])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 54204434HCID 54204434, compound

Product 1

HCID 53840462HCID 53840462, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Anhydrous potassium carbonate (8.89 g) was added to a solution of methyl 2-methoxyimino-3,3-diethoxybutyrate (syn isomer, 10 g) in chloroform (40 ml). Sulfuryl chloride (6.94 g) was added to the suspension at -6° to -2° C. over 50 minutes, and stirred at -5° to -2° C. for 10 minutes. After removing the solvent om the resultant mixture, ethanol (10 ml) was added to the residue and stirred for 30 minutes. Water (25 ml) was added to the mixture, and the mixture was extracted with diisopropyl ether (20 ml) twice. The extract was washed with water (10 ml) and a saturated aqueous solution of sodium chloride (5 ml) subsequently, and dried over magnesium sulfate. The solution was evaporated in vacuo to give methyl 2-methoxyimino-3,3-diethoxy-4-chlorobutyrate (syn isomer, 11.23 g).

Workup

  1. customAfter removing the solvent om the resultant mixture, ethanol (10 ml)
  2. additionwas added to the residue
  3. stirringstirred for 30 minutes
  4. additionWater (25 ml) was added to the mixture
  5. extractionthe mixture was extracted with diisopropyl ether (20 ml) twice
  6. washThe extract was washed with water (10 ml)
  7. dry with materiala saturated aqueous solution of sodium chloride (5 ml) subsequently, and dried over magnesium sulfate
  8. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-1c311ea2d860441291391ede3836ec3d
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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