Reaktion #821525

Reaktionsgleichung

n-BuLi

acetone oxime

Water

methyl 4-bromobenzoate

→

title compound

5-(4-Bromophenyl)-3-methyl isoxazole

Lösungsmittel

—

hexanes

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe organics were extracted
2. 2
   Sonstigeevaporated
3. 3
   Sonstigeto give a brown oil, which
4. 4
   Sonstigewas further evaporated from toluene (2×25 ml)
5. 5
   SonstigeThe crude product was purified by column chromatography (silica gel, 10-25% gradient of EtOAc in hexane)

Vorschrift

A solution of n-BuLi (81 ml of a 1.6M solution in hexanes) was added to a solution of acetone oxime (4.85 g) in THF (100 ml) at 0° C. The reaction mixture was allowed to warm to rt over 1 h. A solution of methyl 4-bromobenzoate (9.4 g) in THF (30 ml) was then added to the reaction mixture and allowed to stir for 24 h. Water (50 ml) was added to the reaction, the organics were extracted and evaporated to give a brown oil, which was further evaporated from toluene (2×25 ml). The crude product was purified by column chromatography (silica gel, 10-25% gradient of EtOAc in hexane) to give the title compound (D39) as a pale yellow solid (5.4 g). LCMS electrospray (+ve) 239 (MH+).

Quelle