Reaktion #42435

Reaktionsgleichung

methyl 1H-indole-5-carboxylate

potassium t-butoxide

1-iodobutane

→

title compound

Methyl 1-butyl-1H-indole-5-carboxylate

Lösungsmittel

methylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethen partitioned between water and methylene chloride
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe organic layer washed three times with brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of methyl 1H-indole-5-carboxylate (6.0 g) in methylsulfoxide (30 mL) was added potassium t-butoxide (3.88 g). The mixture was stirred at room temperature for 10 minutes at which time 1-iodobutane (1.8 mL) was added. The mixture was stirred at room temperature for 5 h then partitioned between water and methylene chloride. The layers were separated and the organic layer washed three times with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 10% ethyl acetate in hexanes as eluent to give 6.18 g of the title compound: 1H NM (CDCl3) δ 0.923, 1.38, 1.83, 3.9, 4.14, 6.58, 7.15, 7.34, 7.9, 8.39.

Quelle