Reaktion #73741

Reaktionsgleichung

n-butyllithium

3′-bromo-2-methoxybiphenyl

1-(2-(benzyloxy)-3-tert-butylphenyl)ethanone

ammonium chloride

→

1-(2-(Benzyloxy)-3-tert-butylphenyl)-1-(2′-methoxybiphenyl-3-yl)ethanol

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not exceed −70° C
2. 2
   Sonstigedid not exceed −65° C
3. 3
   workup.STIRRINGStirring
4. 4
   workup.WAITwas continued at −78° C. for 20 min and at room temperature for 2 hr
5. 5
   Extraktionextracted with ethyl acetate (150 mL)
6. 6
   ExtraktionThe organic extract
7. 7
   Waschenwas washed with water (2×80 mL)
8. 8
   TrocknenThe organic layer was dried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigethe solvent was removed on a rotary evaporator

Vorschrift

A solution of 3′-bromo-2-methoxybiphenyl (1.31 g, 5 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred at −78° C. and 2.5M n-butyllithium in hexanes (2 mL, 5 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 1 hr. A solution of 1-(2-(benzyloxy)-3-tert-butylphenyl)ethanone (1.41 g, 5 mmol) in tetrahydrofuran (8 mL) was added at such a rate that the temperature did not exceed −65° C. Stirring was continued at −78° C. for 20 min and at room temperature for 2 hr. The reaction mixture was poured onto saturated ammonium chloride (80 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed on a rotary evaporator. The crude product 27 was used as such in the next step.

Quelle