Reaktion #167519

Reaktionsgleichung

HCl

ethyl bromofluoroacetate

THF

4′-propyl-[1,1′-bi(cyclohexane)]-4-carboaldehyde

THF

→

ethyl 2-fluoro-3-hydroxy-3-(4′-propyl-[1,1′-bi(cyclohexane)]-4-yl)propanoate

Ausbeute 127.7%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto heating
2. 2
   Temperaturreflux for 4 hours
3. 3
   TemperaturAfter cooling the resultant
4. 4
   Sonstigereaction mixture to 25° C.
5. 5
   Sonstigeto separate the mixture into an organic layer
6. 6
   SonstigeThe resultant organic layer was isolated
7. 7
   Waschenwashed with water
8. 8
   Trocknena saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
10. 10
    Sonstigethe resultant residue was purified by a preparative isolation operation by means of column chromatography
11. 11
    Trocknenethyl acetate=9:1 in a volume ratio) as an eluent and silica gel as a filler, the resultant product was dried

Vorschrift

To a reaction vessel under a nitrogen atmosphere, 1.1 g of well-dried zinc, 2.6 g of ethyl bromofluoroacetate (e-2) and 10 ml of THF were added, and the resultant mixture was cooled to 0° C. and stirred for 1 hour. The solution was slowly added dropwise in a temperature range of 20° C. to 25° C. to another reaction vessel under a nitrogen atmosphere in which 2.0 g of 4′-propyl-[1,1′-bi(cyclohexane)]-4-carboaldehyde (e-1) and 10 ml of THF were put, and the resultant mixture was further subjected to heating reflux for 4 hours. After cooling the resultant reaction mixture to 25° C., 100 ml of 1 N HCl aqueous solution and 100 ml of ethyl acetate were added to separate the mixture into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was isolated, and washed with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, the resultant residue was purified by a preparative isolation operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 in a volume ratio) as an eluent and silica gel as a filler, the resultant product was dried, and thus 3.7 g of ethyl 2-fluoro-3-hydroxy-3-(4′-propyl-[1,1′-bi(cyclohexane)]-4-yl)propanoate (e-3) was obtained.

Quelle