Pyridine → HCID 86634968, compound

HRID 1665217Notes

Reaction equation

HRID 1665217 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.[CH:16]([O:19][NH2:20])([CH3:18])[CH3:17].N1C=CC=CC=1>C(OCC)(=O)C>[CH:16]([O:19][N:20]=[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])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 22820027HCID 22820027, compound

Product 1

HCID 86634968HCID 86634968, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, a mixture of 0.30 g of methyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate, 0.17 g of O-isopropylhydroxylamine hydrochloride and 2 ml of pyridine was stirred at room temperature for 6 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 0.27 g of methyl (1R)-trans-3-[(E)-3-isopropoxyimino-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-dff0aea813b344f580a553f7230e537f
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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