Reaktion #73742

Reaktionsgleichung

27

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

p-toluene sulfonic acid

→

3′-(1-(2-(Benzyloxy)-3-tert-butylphenyl)vinyl)-2-methoxybiphenyl

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed under a Dean-Stark trap for 2 hr
2. 2
   TemperaturAfter cooling the reaction mixture
3. 3
   Waschenwashed with saturated sodium bicarbonate (80 mL) and water (2×80 mL)
4. 4
   TrocknenThe organic layer was dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent was removed on a rotary evaporator
7. 7
   SonstigeThe crude product was purified by chromatography on silica (80 g) with hexane (4 L)
8. 8
   SonstigePure 28 (1.3 g, 58% over 2 steps) was isolated

Vorschrift

A solution of crude 27 (5 mmol) in toluene (120 mL) was treated with p-toluene sulfonic acid (0.2 g) and refluxed under a Dean-Stark trap for 2 hr. After cooling the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (80 mL) and 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 was purified by chromatography on silica (80 g) with hexane (4 L). Pure 28 (1.3 g, 58% over 2 steps) was isolated.

Quelle