Methyl iodide → Indole

Participants

Reaction Steps

To a cold (-78°), stirred solution of 560 mg of ethyl 1-(p-chlorobenzyl)-5-fluoro-3-methylthioindole-2-acetate from Example 3 in 6 75 mL dry tetrahydrofuran, under argon, was added 2.72 mL of a 0.63 M solution of potassium hexamethyldisilazide in toluene. After 2 h at -78°, 123 μL of methyl iodide was added and the mixture stirred at -78° for 30 min and 0° for 1 h. 10% aqueous sodium bisulfate and ether were then added. The organic layer was separated, washed with 10% aqueous sodium bisulfate, water and brine and dried over MgSO4. Filtration and concentration gave a pale yellow oil which was purified by flash chromatography on silica gel. Elution with a mixture of hexane ethyl acetate (85:15) gave an indole derivative, mp 131°-132°.

Provenance & Evidence