Boron trifluoride → HCID 54204434, compound

HRID 463422Notes

Reaction equation

HRID 463422 reaction equation
C([O-])([O-])[O:2][CH2:3][CH3:4].B(F)(F)F.[CH3:11][O:12][N:13]=[C:14]([C:19](=[O:21])[CH3:20])[C:15]([O:17][CH3:18])=[O:16].C(=O)(O)[O-].[Na+].[CH:27](OC(C)C)(C)[CH3:28]>C(O)C>[CH3:11][O:12][N:13]=[C:14]([C:19]([O:2][CH2:3][CH3:4])([O:21][CH2:27][CH3:28])[CH3:20])[C:15]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 5

HCID 6356Boron trifluorideHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 53630039EthylorthoformateHCID 54071723HCID 54071723, compound

Product 1

HCID 54204434HCID 54204434, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl orthoformate (14.0 g) and borontrifluoride diethyletherate (0.45 g) were added to a solution of methyl 2-methoxyimino-3-oxobutyrate (syn isomer, 10 g) in ethanol (20 ml) and stirred at 70° C. for 4 hours. To the resultant mixture were added a saturated aqueous solution of sodium bicarbonate (20 ml) and diisopropyl ether (30 ml). After separating the organic solution, the aqueous solution was extracted with diisopropyl ether (30 ml). The organic layer and the extract were combined, washed with water and a saturated aqueous solution of sodium chloride (30 ml) in turn and dried over magnesium sulfate. The solution was evaporated in vacuo to give methyl 2-methoxyimino-3,3-diethoxybutyrate (syn isomer, 13.9 g.).

Workup

  1. customAfter separating the organic solution
  2. extractionthe aqueous solution was extracted with diisopropyl ether (30 ml)
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride (30 ml) in turn and dried over magnesium sulfate
  5. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-963650220e97440b85eacd1b274f6578
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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