反应详情

Sodium hydride (0.17 g. of 50% dispersion in mineral oil) was added portionwise to a stirred solution of 6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester (0.90 g.) in dry N,N-dimethylformamide (50 ml.) and the mixture was stirred at room temperature for 1 hour. Benzyl bromide (0.61 g.) was added and the resulting mixture was stirred for 2 hours and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed well with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform first gave mineral oil followed by pure product. Evaporation of the product-containing fractions gave a solid which was crystallized from ethyl acetate/petrol (b.p. 60°-80°) to give 1-benzyl-6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester, m.p. 120°-122° C.

1. stirringthe resulting mixture was stirred for 2 hours
2. extractionThe mixture was extracted several times with ethyl acetate
3. washthe combined extracts were washed well with water
4. dry with materialdried (Na2SO4)
5. customEvaporation of the solvent
6. customgave an oil which
7. customwas chromatographed on silica gel
8. washElution with chloroform first gave mineral oil
9. customEvaporation of the product-containing fractions
10. customgave a solid which
11. customwas crystallized from ethyl acetate/petrol (b.p. 60°-80°)