Reaktion #415982

Reaktionsgleichung

hydrogen

1-iodo-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane

hydrochloric acid

sodium hydride

dimethyl-2-methylsulfonyl-azelate

→

title compound

Ausbeute 88.0%

Methyl 8-methylsulfonyl-8-methoxycarbonyl-12-acetoxy-13-(3-trifluoromethylphenoxy)tridecanoate

Ausbeute 88.0%

Lösungsmittel

water

ether

dimethylformamide

—

petroleum ether

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto precipitate sodium iodide which
2. 2
   Sonstigeis removed by filtration
3. 3
   EinengenThe filtrate is concentrated in vacuo
4. 4
   Sonstigeto give a residue which
5. 5
   Extraktionextracted with ether
6. 6
   WaschenThe ether extracts are washed with water until neutral,
7. 7
   Trocknendried over anhydrous magensium sulfate
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A 50% oil dispersion of sodium hydride (2.11 g., 0.044 mole) in mineral oil is washed with petroleum ether and then suspended in dry dimethylformamide (30 ml.) under a nitrogen atmosphere at room temperature. To this suspension is added a solution of dimethyl-2-methylsulfonyl-azelate (11.8 g., 0.04 mole) in dry dimethylformamide (30 ml.). After the evolution of hydrogen is completed, the mixture is cooled to 5° C. in an ice bath and a solution of 1-iodo-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane (18.3 g., 0.044 mole) in dry dimethylformamide (30 ml.) is added dropwise. After 48 hours, ether is added to the reaction mixture to precipitate sodium iodide which is removed by filtration. The filtrate is concentrated in vacuo to give a residue which is diluted with water, acidified with 6N hydrochloric acid, and extracted with ether. The ether extracts are washed with water until neutral, dried over anhydrous magensium sulfate, and concentrated in vacuo to give the title compound (20.5 g., 0.035 mole, 88%).

Quelle