Imidazole → HCID 14234521, compound

Participants

Reaction Steps

To a solution of 37 g. (0.253 m) of methyl 3-(R)-methyl-5-hydroxypentanoate and 37 g. (0.543 m) of imidazole in 500 ml. of dimethylformamide was added 37 g. (0.249 m) of t-butyldimethylsilyl chloride and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted (4×100 ml.) with ether. The combined extracts were washed with 10% hydrochloric acid, a saturated sodium bicarbonate solution, water and a brine solution, and dried over magnesium sulfate. Removal of the solvent gave 121.88 g. of crude product which, on distillation, gave 107.12 g. of pure product, b.p. 80°-81° C./0.4 torr.

Provenance & Evidence