Sodium Hydroxide → HCID 22718489, compound

Participants

Reaction Steps

A solution of 0.1 g of ethyl 5-(3,5-dichlorophenylsulphanyl)-4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate in 2 ml of anhydrous tetrahydroftiran was stirred at room temperature under nitrogen and treated with 65 mg of 4-bromomethylpyridine hydrobromide, 5 mg of tetra-n-butylammonium bromide and 24 mg of powdered sodium hydroxide. The mixture was stirred at room temperature for 20 h then diluted with 20 ml of water and extracted three times with 10 ml of ethyl acetate. Combined extracts were washed with 10 ml of brine, then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/isohexane (1:1) for the elution to give 0.104 g of ethyl 5-(3,5-dichlorophenylsulphanyl)-4-isopropyl-2-methyl-1-pyridin-4-yl-1H-pyrrole-3-carboxylate as a colourless gum. Mass spectrum (ESI) m/z 463 [M+H]+. 1H NMR (CDCl3) 1.32 (d, 6H), 1.40 (t, 3H), 2.45 (s, 3H), 3.61 (m 1H), 4.34 (q, 2H), 5.16 (s, 2H), 6.69 (d, 2H), 6.76 (m, 2H), 7.01 (t, 1H), 8.47 (m, 2H).

Provenance & Evidence