Reaktion #44784

Reaktionsgleichung

2-(4-iodophenyl)oxazole

4-methoxybenzyl zinc chloride

→

2-[4-[(4-methoxyphenyl)methyl]phenyl]oxazole

Ausbeute 81.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe filtrate was concentrated
2. 2
   workup.ADDITIONThe resulting solid was treated with a mixture of ethyl acetate
3. 3
   FiltrationThe mixture was filtered
4. 4
   Sonstigethe organic layer was dried
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification on silica gel using a gradient of dichloromethane in hexane

Vorschrift

A Schlenk Flask was charged with tetrakis(triphenylphosphine)palladium(0) (0.42 g, 0.37 mmol), nitrogen, THF (20 ML), 2-(4-iodophenyl)oxazole (1 g, 3.7 mmol), and 4-methoxybenzyl zinc chloride (0.5 M in THF, 9.6 mL, 4.8 mmol). After 3 hours, the filtrate was concentrated. The resulting solid was treated with a mixture of ethyl acetate and a dilute aqueous ammonium chloride solution. The mixture was filtered and the organic layer was dried and concentrated. Purification on silica gel using a gradient of dichloromethane in hexane gave 0.8 g of 2-[4-[(4-methoxyphenyl)methyl]phenyl]oxazole, 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.22 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 3.96 (s, 2H), 3.78 (s, 3H).

Quelle