Hydrochloric Acid → Cyclopentyl[4-(trifluoromethyl)phenyl]methanone

HRID 735890

Reaktionsgleichung

Reaktionsgleichung von HRID 735890
CON(C)[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.[CH:17]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18]1.N#N.Cl>C1COCC1>[CH:17]1([C:4]([C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=2)=[O:15])[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamideHCID 178419650HCID 178419650, Verbindung

Produkt 1

HCID 24724174Cyclopentyl[4-(trifluoromethyl)phenyl]methanoneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of N-methoxy-N-methyl-4-(trifluoromethyl)benzamide (3.44 g, 14.75 mmol) in anhydrous THF (70 mL) was added dropwise over a period of 30 minutes a solution of cyclopentylmagnesium bromide (2 M in diethyl ether, 29.5 mmol, 14.75 mL) under inert atmosphere of N2. The reaction mixture was slowly allowed to warm to rt overnight. An aqueous solution of HCl (1N, 50 mL) was added and the resulting mixture was extracted with diethyl ether (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over MgSO4, filtered and evaporated under vacuum to give a brown oil (3.0 g). Purification by chromatography (SiO2, DCM/c-Hex 1/3) gave the title compound as a colorless oil (610 mg, 17%). 1H NMR (CDCl3, 300 MHz) δ 8.24 (d, J=8.1 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 3.96-3.79 (m, 1H), 2.21-2.00 (m, 4H), 2.01-1.71 (m, 4H). HPLC (Condition A), Rt: 5.22 min (HPLC purity: 98.6%).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethyl ether (3×50 mL)
  2. washThe combined organic layers were washed with brine (1×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5c4328da20c542e39e7ac026782bbbf3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592477B2

Verknüpfte Notizen

Wird geladen…