Water → HCID 53939913, compound

HRID 1982024Notes

Reaction equation

HRID 1982024 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-77ab79dbbbd64dfe96f6dbff4881f0ed
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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