O-ethylhydroxylamine hydrochloride → HCID 136127124, compound

HRID 1780619Notes

Reaction equation

HRID 1780619 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[C:7]([CH3:25])=[C:8]([CH3:24])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[C:15]([C:19](=O)[CH2:20][CH3:21])=[C:14]([OH:23])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1.C([O-])(=O)C.[Na+].Cl.[CH2:33]([O:35][NH2:36])[CH3:34]>C(O)C>[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[C:7]([CH3:25])=[C:8]([CH3:24])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[C:15]([C:19](=[N:36][O:35][CH2:33][CH3:34])[CH2:20][CH3:21])=[C:14]([OH:23])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458831HCID 178458831, compound

Product 1

HCID 136127124HCID 136127124, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution 0.3 g of the 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-propionyl-3-hydroxycyclohex-2-en-1-one in 10 ml of ethanol was added 0.14 g of sodium acetate and 0.09 g of ethoxyamine hydrochloric acid. After stirring at room temperature for 20 hours, the reaction mixture was quenched with 20 ml water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under the reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 0.28 g of 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one as yellow oil.

Workup

  1. customthe reaction mixture was quenched with 20 ml water
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under the reduced pressure
  6. customto afford a crude product
  7. customFinal purification

Sources & evidence

ORD record
ord-fb17c80804aa4773bb92aa59af637dea
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

Loading…