Réaction #1483073

Équation de réaction

water

acetyl chloride

aluminum chloride

1H-indole-6-carboxylic acid methyl ester

→

3-acetyl-1H-indole-6-carboxylic acid methyl ester

Rendement 99.7%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Extractionthis was extracted with ethyl acetate (300 mL)
3. 3
   SéchageThe organic layer was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Mode opératoire

To a solution of acetyl chloride (0.23 mL, 3.3 mmole) and aluminum chloride (0.88 g, 6.6 mmol) in methylene chloride (30 mL) was added 1H-indole-6-carboxylic acid methyl ester (0.53 g, 3.0 mmol). After stirring 1 hr at room temperature water (300 mL) was added and then this was extracted with ethyl acetate (300 mL). The organic layer was dried (MgSO4), filtered and concentrated to collect 0.65 g (99% yield) of 3-acetyl-1H-indole-6-carboxylic acid methyl ester a light yellow solid. 1H NMR (300 MHz, DMSO) δ 12.27 (s, 1H), 8.52 (s, 1H), 8.24 (d, 1H, J=8.2 Hz), 8.08 (d, 1H, J=1.0 Hz), 7.78 (dd, 1H, J=8.2, 1.0 Hz), 3.86 (s, 3H), 2.47 (s, 3H).

Source