Potassium Carbonate → (R)-3-(4-Trifluoromethylphenyl)-butyramide

HRID 1503187

Reaktionsgleichung

Reaktionsgleichung von HRID 1503187
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[C:20]([NH2:25])(=[O:24])[CH:21]=[CH:22][CH3:23].O1CCOCC1>C/C(/O)=C/C(C)=O.C=C.C=C.[Rh].O>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C@H:22]([CH3:23])[CH2:21][C:20]([NH2:25])=[O:24])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 31877But-2-enamideHCID 27343894-(Trifluoromethyl)phenylboronic acid

Produkt 1

HCID 44236521(R)-3-(4-Trifluoromethylphenyl)-butyramide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11010647ethene;(Z)-4-hydroxypent-3-en-2-one;rhodiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Acetylacetonatobis(ethylene)rhodium(I) (0.3 mmol), (S)-(−)-2,2′-Bis(diphenyl-phosphino)-1,1′-binaphthalene (0.045 mmol), 4-(trifluoromethyl)phenylboronic acid (2 mmol), K2CO3 (0.5 mmol), and but-2-enoic acid amide (1 mmol) are added into a 25-mL round-bottomed flask containing a magnetic stirrer bar, a septum inlet, and a reflux condenser. The flask is flashed with argon and then charged with 1,4-dioxane (3 mL) and de-ionized H2O (0.5 mL). The reaction mixture is stirred for 16 hours at 100° C. The (R)-3-(4-trifluoromethylphenyl)butyramide is extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. Chromatography over silica gel gives the desired product.

Aufarbeitung

  1. additioncontaining a magnetic stirrer bar, a septum inlet, and a reflux condenser
  2. extractionThe (R)-3-(4-trifluoromethylphenyl)butyramide is extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-25cbbc5fb0df44abbbf20ef9ab9b1028
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212155B2

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