Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochloride → 2-(3-Chloroallyloxyaminobutylidene)-5-(3-methyl-4-ethyl-6-isobutoxytetrahydropyran-2-yl)-cyclohexane-1,3-dione

HRID 746124Notes

Reaction equation

HRID 746124 reaction equation
[C:1]([CH:6]1[C:11](=[O:12])[CH2:10][CH:9]([CH:13]2[CH:18]([CH3:19])[CH:17]([CH2:20][CH3:21])[CH2:16][CH:15]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])[O:14]2)[CH2:8][C:7]1=[O:27])(=O)[CH2:2][CH2:3][CH3:4].Cl.[Cl:29][CH:30]=[CH:31][CH2:32][O:33][NH2:34]>C(O)C.C([O-])(=O)C.[Na+]>[Cl:29][CH:30]=[CH:31][CH2:32][O:33][NH:34][CH2:4][CH2:3][CH2:2][CH:1]=[C:6]1[C:7](=[O:27])[CH2:8][CH:9]([CH:13]2[CH:18]([CH3:19])[CH:17]([CH2:20][CH3:21])[CH2:16][CH:15]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])[O:14]2)[CH2:10][C:11]1=[O:12]

Participants

5

Reactant 2

HCID 158057Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochlorideHCID 134214452-Butyryl-5-(3-methyl-4-ethyl-6-isobutoxytetrahydropyran-2-yl)-cyclohexane-1,3-dione

Product 1

HCID 543533332-(3-Chloroallyloxyaminobutylidene)-5-(3-methyl-4-ethyl-6-isobutoxytetrahydropyran-2-yl)-cyclohexane-1,3-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 517045Sodium AcetateSolvent

Procedure

10.2 parts by weight of 2-butyryl-5-(3-methyl-4-ethyl-6-isobutoxytetrahydropyran-2-yl)-cyclohexane-1,3-dione were dissolved in 100 parts by volume of ethanol, and 2.42 parts by weight of sodium acetate and 3.86 parts by weight of O-(3-chloroallyl)-hydroxylamine hydrochloride were added. The mixture was stirred for several hours at room temperature and then poured into ice-water, and the resulting mixture was extracted with methylene chloride. The methylene chloride phase was evaporated off, leaving 11.1 parts by weight of 2-(3-chloroallyloxyaminobutylidene)-5-(3-methyl-4-ethyl-6-isobutoxytetrahydropyran-2-yl)-cyclohexane-1,3-dione as a yellow oil of refractive index nD22 1.5129.

Workup

  1. additionwere added
  2. extractionthe resulting mixture was extracted with methylene chloride
  3. customThe methylene chloride phase was evaporated off

Sources & evidence

ORD record
ord-2679ef3b0ea54d12a1196452c5a1ec3e
Source dataset
uspto-grants-1986_07
Patent number
US04602935

Reaction notes

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