O-ethylhydroxylamine hydrochloride → HCID 136200006, compound

HRID 1870641Notes

Reaction equation

HRID 1870641 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]1[CH2:21][C:20](=[O:22])[C:19]([C:23](=O)[CH2:24][CH3:25])=[CH:18][CH2:17]1.C([O-])(=[O:29])C.[Na+].Cl.[O:33]([NH2:36])[CH2:34][CH3:35]>C(O)C>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]1[CH2:17][C:18](=[O:29])[C:19]([C:23](=[N:36][O:33][CH2:34][CH3:35])[CH2:24][CH3:25])=[C:20]([OH:22])[CH2:21]1

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 18696693HCID 18696693, compound

Product 1

HCID 136200006HCID 136200006, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution 0.15 g of the 5-(6-chloro-2-ethyl-2,4,7-trimethylindan-5-yl)-2-propionyl-cyclohex-2-en-1-one in 10 ml of ethanol was added 0.9 g of sodium acetate (NaOAc.3H2O) and 0.64 g of ethoxylamine hydrochloride. After stirring at room temperature for 10 hours, the reaction mixture extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 0.1153 g of the title compound as yellow oil.

Workup

  1. extractionthe reaction mixture extracted with diethyl ether
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-64bcff8be30e4874bcb3dd692e943e86
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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