Imidazole → HCID 131718791, compound

Participants

Reaction Steps

To a solution of 37.23 g (0.157 mol) of the crude 2-hydroxy-3-(3-hydroxy-1-propyl)-4-(3-pyridyl)-γ-butyrolactone in 170 ml of dimethylformide are added 21.4 g (0.157 mol) of imidazole and 23.63 g (0.157 mol) of t-butyldiphenylchlorosilane and the mixture is stirred at room temperature overnight. The mixture is diluted with ethyl acetate and washed with water (2×), brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography from silica gel using ethyl acetate:methylene chloride (1:1) as eluent to give 3-[3-(t-butyldiphenylsilyloxy)-1-propyl]-2-hydroxy-4-(3-pyridyl)-γ-butylactone which crystallizes from ether-petroleum ether and having mp 81°-84° C. and elemental analysis: C, 61,52; H, 8.21; N, 3.91 (theory, C, 61.50; H, 8.32; N, 3.98).

Provenance & Evidence