Réaction #42435

Équation de réaction

methyl 1H-indole-5-carboxylate

potassium t-butoxide

1-iodobutane

→

title compound

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

Solvants

methylsulfoxide

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autrethen partitioned between water and methylene chloride
3. 3
   AutreThe layers were separated
4. 4
   Lavagethe organic layer washed three times with brine
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

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.

Source