Methanol → HCID 54165460, compound

HRID 1154803Notes

Reaction equation

HRID 1154803 reaction equation
[CH:1]([O-])([O-])[O:2]C.[CH3:6][O:7][N:8]=[C:9]([C:15](=[O:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:18]O>>[CH3:6][O:7][N:8]=[C:9]([C:15]([O:2][CH3:1])([O:17][CH3:18])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoateHCID 53629101Methylorthoformate2×

Product 1

HCID 54165460HCID 54165460, compound

Procedure

Methyl orthoformate (31.8 g) and "Amberlist 15" (trademark) (1.7 g) were added to a stirred solution of ethyl 2-methoxyimino-3-oxobutyrate (syn isomer, 17.3 g) in dry methanol (50 ml) and stirred at 50° to 60° C. for 2.5 hours. To the resultant solution was added methyl orthoformate (10.6 g) and stirred for 2 hours. The solution was allowed to stand in refrigerator overnight and stirred at 50° to 60° C. for 2 hours. After evaporating methanol in vacuo, diethyl ether (100 ml) and water (50 ml) were added to the residue, and the organic layer was separated. The aqueous layer was extracted with diethyl ether. The organic layer and the extract were combined together and washed with a saturated aqueous solution of sodium chloride. The solution was dried over magnesium sulfate and evaporated under reduced pressure to give ethyl 2-methoxyimino-3,3-dimethoxybutyrate (syn isomer, 18 g). bp 61° to 64° C./0.35 mmHg.

Workup

  1. stirringstirred for 2 hours
  2. customto stand in refrigerator overnight
  3. stirringstirred at 50° to 60° C. for 2 hours
  4. customAfter evaporating methanol in vacuo, diethyl ether (100 ml) and water (50 ml)
  5. additionwere added to the residue
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with diethyl ether
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialThe solution was dried over magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5687e4bc466149b187c40d1a251f32bd
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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