Reaktion #1074344

Reaktionsgleichung

hydride

lithium aluminium hydride

iodide

KHMDS

ethyl iodide

benzyl bromide

sodium hydride

( 2 )

2,4-bis(1,1-Dimethypropyl)phenoxyacetic Acid

Indol-2-carboxylic acid ethyl ester

→

indole

Lösungsmittel

THF

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C.

Vorschrift

Aldehyde IX is prepared from Indol-2-carboxylic acid ethyl ester I in two steps: (1) Reduction with lithium aluminium hydride or other hydride in a suitable solvent such as THF at 0° C. and (2) oxidation with an oxidizing reagent such as manganese dioxide in a solvent such as THF. Aldehyde IX can be alkylated by a suitable alkyl bromide (or iodide), such as benzyl bromide or ethyl iodide in the presence of a strong base such as sodium hydride or KHMDS in a solvent such as DMF to yield indole X. Indole X can be converted to an unsaturated acid XI in two steps: (1) Wittig reaction with a suitable reagent such as trimethyl phosphonoacetate in the presence of a base such as sodium hydride in a solvent such as THF and (2) Hydrolysis by aqueous sodium hydroxide.

Quelle