Reaktion #73720

Reaktionsgleichung

(2-(benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone

phenyllithium

ammonium chloride

→

6

Ausbeute 100.1%

(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol

Ausbeute 100.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not exceed −70° C
2. 2
   Extraktionextracted with ethyl acetate (150 mL)
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with water (2×100 mL)
5. 5
   Trocknendried over sodium sulfate
6. 6
   SonstigeThe crude product was purified by chromatography on silica (60 g) with 5% ethyl acetate in heptane (1 L)

Vorschrift

A solution of (2-(benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone (0.96 g, 2.28 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred at −78° C. under nitrogen and 1.8 M phenyllithium (2 mL, 3.6 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 30 min for 1 hr at room temperature. The reaction mixture was poured on saturated ammonium chloride (150 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×100 mL), dried over sodium sulfate and stripped. The crude product was purified by chromatography on silica (60 g) with 5% ethyl acetate in heptane (1 L), then 7.5% (2 L) to afford 6 (1.14 g, 100%). This material contains a minor impurity and it was used as such in the next step.

Quelle