Pyridine → HCID 86634963, compound

HRID 1665213Notes

Reaction equation

HRID 1665213 reaction equation
[CH3:1][C:2]1([CH3:14])[C@H:4](/[CH:5]=[C:6](\[CH3:9])/[CH:7]=O)[C@H:3]1[C:10]([O:12][CH3:13])=[O:11].Cl.[CH2:16]([O:18][NH2:19])[CH3:17].N1C=CC=CC=1>C(OCC)(=O)C>[CH2:16]([O:18][N:19]=[CH:7]/[C:6](/[CH3:9])=[CH:5]/[C@@H:4]1[C@@H:3]([C:10]([O:12][CH3:13])=[O:11])[C:2]1([CH3:14])[CH3:1])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 22820027HCID 22820027, compound

Product 1

HCID 86634963HCID 86634963, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, a mixture of 0.94 g of methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate, 0.47 g of O-ethylhydroxylamine hydrochloride and 2 ml of pyridine was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture, and the mixture was washed with 1 mol/L hydrochloric acid and saturated brine respectively. The organic layer was dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.92 g of methyl (1R)-trans-3-[(E)-3-ethoxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate:

Workup

  1. washthe mixture was washed with 1 mol/L hydrochloric acid and saturated brine respectively
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-481a39d7ba5c470da9383dab5c362a25
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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