Imidazole → (R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid

Participants

Reaction Steps

A mixture of 2.44 g (R)-3-hydroxytetradecanoic acid (0.01 mole), 2.72 g imidazole (0.04 mole), 3.03 g t-butyldimethylsilyl chloride (0.02 mole), and 50 mL dichloromethane was stirred at room temperature for 22 hours. 5 mL Methanol was added and the resultant mixture was stirred at room temperature for 15 minutes after which it was concentrated to dryness on a rotary evaporator (ca. 100 mm Hg, 35° C.). The residue was chromatographed on a 1" column slurry packed with silica gel in chloroform. The product was eluted with 5% methanol in chloroform. The chromatography was monitored by TLC (silica gel, 5% methanol in chloroform, phosphomolybdic acid visualization, product Rf ca. 0.6) and fractions containing only product were pooled and concentrated on a rotary evaporator (ca. 1 mm Hg, 30° C.) to a clear oil (2.84 g, 79% yield).

Provenance & Evidence