Reaktion #507980

Reaktionsgleichung

1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester

Compound 1

1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester

diisopropylethylamine

chloromethyl methyl ether

DMF

→

1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxylic acid, ethyl ester

Compound 2

1-Benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxylic Acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under vacuum
2. 2
   Sonstigepurified by flash chromatography on silica gel eluting with 10-20% EtOAc-hexanes

Vorschrift

To a solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 1, 345 mg, 1.0 mmol) in DMF (2 ml) was added diisopropylethylamine (iPr2NEt, 1.7 ml, 10.0 mmol) and chloromethyl methyl ether (MOMCl, 0.38 ml, 5.0 mmol). The mixture was stirred at room temperature for 72 h, and concentrated under vacuum, and purified by flash chromatography on silica gel eluting with 10-20% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 2) as a clear oil.

Quelle