Reaktion #1827930

Reaktionsgleichung

methyl 4-bromocrotonate

1-Acetyl-6-bromo-5-hydroxyindoline

sodium hydride

→

title compound

Ausbeute 68.0%

Methyl 4-[(1-acetyl-6-bromoindolin-5-yl)oxy]crotonate

Ausbeute 68.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added over 10 min
2. 2
   Temperaturcooled
3. 3
   FiltrationThe precipitated material was filtered off
4. 4
   Waschenwashed with water and ether

Vorschrift

1-Acetyl-6-bromo-5-hydroxyindoline (Tetrahedron, 1973, 29 (8), 1115) (2.54 g, 10 mmol) was stirred under Ar in dry DMF (50 ml) as sodium hydride (80%, 0.33 g, 11 mmol) was added over 10 min. After a further 10 min, methyl 4-bromocrotonate (1.75 ml, 15 mmol) was added. The mixture was stirred at 60° C. for 2 h, cooled, and diluted with water. The precipitated material was filtered off and washed with water and ether, affording the title compound (2.40 g, 68%) as a brown solid. NMR showed a mixture of isomers (ca. 1:1).

Quelle