Potassium Hydroxide → methyl 1-cyclohexylmethyl-3-methyl-1H-indole-6-carboxylate

Participants

Reaction Steps

A mixture of methyl 3-methyl-1H-indole-6-carboxylate(10 g, Reference Example 30), cyclohexylmethylbromide (19 g), potassium hydroxide (12 g) and sodium iodide (0.1 g) in acetone (200 ml) was stirred at room temperature for 6 hours. The reaction mixture was evaporated. The residue was partitioned between ethyl acetate (250 ml) and water (250 ml). The aqueous layer was extracted three times with ethyl acetate (250 ml). The total combined organic phases were dried over sodium sulphate then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (gradient elution, 0:10 to 1:9, v/v)to yield the title compound (9.5 g). NMR (CDCl3): δ 0.90-1.10(m), 1.10-1.40(m), 1.60-1.90(m), 2.30(s), 3.90-4.00(m), 3.90(s), 7.00(s), 7.50-7.60(m), 7.70-7.80(m), 8.00(s). MH+ 271.

Provenance & Evidence