Ethanol → 1-(1,2,3,5,6,7-Hexahydro-s-indacen-4-yl)-ethanone oxide

HRID 2303595Notes

Reaction equation

HRID 2303595 reaction equation
[CH2:1]1[C:12]2[C:4](=[C:5]([C:13](=[O:15])[CH3:14])[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.C([OH:18])C>N1C=CC=CC=1>[CH2:9]1[C:10]2[C:6](=[C:5]([C:13](=[O+:15][O-:18])[CH3:14])[C:4]3[CH2:3][CH2:2][CH2:1][C:12]=3[CH:11]=2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 702EthanolHCID 3826691-(1,2,3,5,6,7-Hexahydro-s-indacen-4-yl)ethanone

Product 1

HCID 867561501-(1,2,3,5,6,7-Hexahydro-s-indacen-4-yl)-ethanone oxideYield 89.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-ethanone (33 grams), ethanol (250 mL) hydroxylamine hydrochloride (58.5 grams) and pyridine (80 mL) was heated to reflux for a period of 12 hours. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was then treated with 500 mL of water and extracted with chloroform-methanol. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to afford 32 grams of the title compound as a mixture of E and Z isomers, 178.6-182.3° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for a period of 12 hours
  3. concentrationconcentrated in vacuo
  4. additionThe residue was then treated with 500 mL of water
  5. extractionextracted with chloroform-methanol
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d35e7bdbdbbb47f7bd15d70e6ac82f96
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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