Water → HCID 54511971, compound

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Reaction Steps

A stirred suspension containing 5-(carboxypentyl) triphenylphosphonium bromide (22 g, 0.048 mol) in dry tetrahydrofuran (100 ml) at 0° C. under a nitrogen atmosphere was treated with potassium t-butoxide (11.2 g, 0.10 mol) and stirred for 2 hours at room temperature. The resulting orange mixture was cooled to 0° C. and treated with a solution of 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone (as prepared in Example 1c, 6.4 g, 0.025 mol) in dry tetrahydrofuran (25 ml). The reaction mixture was stirred at room temperature for 4 hours after which time the solvent was evaporated off under reduced pressure to yield a residue which was treated with water (200 ml) and extracted with ethyl acetate (4×150 ml). The aqueous solution was acidified to pH 1 using 12M hydrochloric acid washed with ethyl acetate (3×100 ml), basified to pH 5.5 using sodium bicarbonate and extracted with ethyl acetate (4×150 ml). The extracts were combined, washed with water then brine, dried over sodium sulfate and the solvent was evaporated off under reduced pressure to yield a crude product. The crude product was purified by column chromatography (silica gel, 5% ethanol in chloroform) to yield an isomeric mixture of E- and Z-8-(1-H-imidazol-1-yl)-7-[[(4-methoxyphenyl)methoxy]methyl]-6-octenoic acid as a pale yellow oil having the following structural characteristics:

Provenance & Evidence