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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 406373Erstellt: 25. Oktober 2026

Ethyl Acetate → 5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrile

https://huagongshe.com/reaction/406373

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthyl AcetateHCID 8857—
EduktMethyl dichlorophosphateHCID 69611—
Edukt1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Edukt5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amideHCID 66630138—
LösungsmittelDichloromethaneHCID 6344—
LösungsmittelHeptaneHCID 8900—
Produkt5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrileHCID 6677801197,3%

Reaktionsschritte

5-(tert-Butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide (640 mg) was dissolved in methylene chloride (13 mL), and 1,8-diazabicyclo[5,4,0]undec-7-ene (862 μL) and methyl dichlorophosphate (301 μL) were added at 0° C. After stirring at room temperature for 1.5 hours, the reaction was terminated with a saturated sodium bicarbonate aqueous solution. The organic layer was washed with brine and then dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was allowed to pass through a silica gel pad (mobile phase:ethyl acetate:heptane=1:2) to obtain the title compound (600 mg).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08754100B2
Quelldatensatzuspto-grants-2014_06
ORD IDord-0c8a6ef0d45e484282c68aa172cda9a4
Quellennotizuspto-grants-2014_06