Water → HCID 86634965, compound

HRID 1665215Notes

Reaction equation

HRID 1665215 reaction equation
[CH3:1][C:2]1([CH3:17])[C@H:4](/[CH:5]=[C:6](\[CH3:9])/[CH:7]=O)[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].Cl.[NH2:19][OH:20].N1C=CC=CC=1.O>C(OCC)(=O)C.O1CCOCC1>[OH:20][N:19]=[CH:7]/[C:6](/[CH3:9])=[CH:5]/[C@@H:4]1[C@@H:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:2]1([CH3:17])[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86634966HCID 86634966, compound

Product 1

HCID 86634965HCID 86634965, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Under nitrogen atmosphere, a mixture of 1.0 g of t-butyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylate, 0.29 g of hydroxylamine hydrochloride, 5 ml of pyridine, 5 ml of water and 30 ml of 1,4-dioxane was stirred at room temperature for 3 hours. 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 0.71 g of t-butyl (1R)-trans-3-[(E)-3-hydroxyimino-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-30453fe51055419c9096530838377739
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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