Water → HCID 53939913, compound

HRID 463394Notes

Reaction equation

HRID 463394 reaction equation
[BrH:1].[NH+]1C=CC=CC=1.[CH3:8][O:9][N:10]=[C:11]([C:17]([O:21][CH3:22])([O:19][CH3:20])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13].O>O1CCCC1>[CH2:15]([O:14][C:12](=[O:13])[C:11](=[N:10][O:9][CH3:8])[C:17]([O:21][CH3:22])([O:19][CH3:20])[CH2:18][Br:1])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 21226041Pyridinium hydrobromideHCID 54165460HCID 54165460, compound

Product 1

HCID 53939913HCID 53939913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridinium hydrobromide perbromide (1.82 g) was added to a solution of ethyl 2-methoxyimino-3,3-dimethoxybutyrate (syn isomer, 1.0 g) in dry tetrahydrofuran (10 ml) and heated under reflux for an hour. The resultant solution was poured into water (30 ml) and extracted with diethyl ether (10 ml×2). The extract was washed with 5% aqueous sodium thiosulfate solution (5 ml×5) and a saturated aqueous solution of sodium chloride (10 ml×1) successively. The solution was dried over magnesium sulfate and evaporated under reduced pressure to give ethyl-2-methoxyimino-3,3-dimethoxy-4-bromobutyrate (syn isomer, 2.02 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for an hour
  3. extractionextracted with diethyl ether (10 ml×2)
  4. washThe extract was washed with 5% aqueous sodium thiosulfate solution (5 ml×5)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f4bc4a8622e144d6810bd8801cd3bea2
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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