Boron trifluoride → HCID 54204434, compound

HRID 1154833Notes

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

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

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

Sources & evidence

ORD record: ord-e0a0f81330fd4dbf92652b47d6c8564d
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298529

Reaction notes

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