Reaktion #1475821

Reaktionsgleichung

5,5-dimethyl-3-hydroxy-2-propionylcyclohex-2-en-1-one

O-[(5-chlorothien-2-yl)methyl]hydroxylamine

→

2-{1-[(5-chlorothien-2-ylmethoxy)imino]propyl}-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one

Ausbeute 70.2%

Lösungsmittel

methylene chloride

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was then evaporated
2. 2
   Sonstigeto remove the ethanol
3. 3
   Sonstigeaffording a thick syrup
4. 4
   Extraktionextracted twice with aqueous 5% wt. sodium hydroxide
5. 5
   SonstigeThe aqueous layer was separated
6. 6
   Extraktionextracted twice with methylene chloride
7. 7
   SonstigeThe methylene chloride layer was separated
8. 8
   Trocknendried with magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    SonstigeThe filtrate was evaporated under vacuum
11. 11
    Sonstigeaffording a viscous liquid which
12. 12
    Sonstigewas then purified via column chromatography
13. 13
    Wascheneluting with tetrahydrofuran-hexane (1:2 vol. ratio)

Vorschrift

In this example, a mixture containing 4.0 gms (0.02 mol) of 5,5-dimethyl-3-hydroxy-2-propionylcyclohex-2-en-1-one and 3.6 gms (0.022 mol) of O-[(5-chlorothien-2-yl)methyl]hydroxylamine in 75 mls of ethanol was stirred at room temperature for about 12 hours. The mixture was then evaporated to remove the ethanol, affording a thick syrup. The syrup was then dissolved in methylene chloride and extracted twice with aqueous 5% wt. sodium hydroxide. The aqueous layer was separated and acidified with concentrated hydrochloric acid and then extracted twice with methylene chloride. The methylene chloride layer was separated, dried with magnesium sulfate, and filtered. The filtrate was evaporated under vacuum, affording a viscous liquid which was then purified via column chromatography eluting with tetrahydrofuran-hexane (1:2 vol. ratio) affording 4.8 gms of 2-{1-[(5-chlorothien-2-ylmethoxy)imino]propyl}-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one.

Quelle