5-Bromo-2-methoxypyridine → 1-(6-Methoxypyridin-3-yl)-4-(trifluoromethyl)cyclohexanol

HRID 1669646

Reaktionsgleichung

C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1.[F:15][C:16]([F:25])([F:24])[CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1>C1COCC1>[CH3:14][O:13][C:10]1[N:11]=[CH:12][C:7]([C:20]2([OH:23])[CH2:19][CH2:18][CH:17]([C:16]([F:24])([F:25])[F:15])[CH2:22][CH2:21]2)=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

n-Butyllithium (3 mL of a 2.5 M solution in hexanes, 7.5 mmol) was added dropwise to 5-bromo-2-methoxy pyridine (6.0 mmol, 0.78 mL) in 40 mL of THF cooled in a dry ice/acetone bath. After aging for 15 min, 4-trifluoromethylcyclohexanone (6.0 mmol, 1 g) was added and the reaction mixture was allowed to slowly warm to 0° C. over 2 h. The reaction was cooled in a dry ice/acetone bath and the reaction was quenched by addition of sat. ammonium chloride (aq), then saturated sodium bicarbonate (aq). The reaction mixture was extracted with hexanes/EtOAc. The organic phase was concentrated and the resultant residue was purified by flash chromatography on silica gel using a step gradient of 4:1, 2:1 and 1:1 (v/v) EtOAc/hexanes to give the title compound as a mixture of isomers. LC-MS (ESI): m/z=276.2 [M+1]+.

Aufarbeitung

temperaturecooled in a dry ice/acetone bath
temperatureThe reaction was cooled in a dry ice/acetone bath
customthe reaction was quenched by addition of sat. ammonium chloride (aq)
extractionThe reaction mixture was extracted with hexanes/EtOAc
concentrationThe organic phase was concentrated
customthe resultant residue was purified by flash chromatography on silica gel using a step gradient of 4:1, 2:1 and 1:1 (v/v) EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-3a86f9390fc64fbb9c926d4849ab3d1d
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07989472B2

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