Ethanol → Ethyl 2-methoxyimino-5-methyl-4-oxohexanoate

HRID 251951Notes

Reaction equation

HRID 251951 reaction equation
[OH:1][C:2]([CH:11]([CH3:13])[CH3:12])=[CH:3][C:4](=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[CH3:15][O:16][NH2:17].C(O)C>C(OCC)(=O)C>[CH3:15][O:16][N:17]=[C:4]([CH2:3][C:2](=[O:1])[CH:11]([CH3:13])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178473097HCID 178473097, compound

Product 1

HCID 86632548Ethyl 2-methoxyimino-5-methyl-4-oxohexanoateYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.0 g of ethyl 4-hydroxy-5-methyl-2-oxo-3-hexenoate, 2.46 g of O-methylhydroxylamine hydrochloride and 10 ml of ethanol was stirred at room temperature for 6 hours. After ethyl acetate was poured into the reaction mixture, the organic layer was washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 5.32 g of ethyl 2-methoxyimino-5-methyl-4-oxohexanoate of the formula:

Workup

  1. washthe organic layer was washed with water
  2. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ac0103fd2954689a164b080008c8f22
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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