Iodine → HCID 86691649, compound

Participants

Reaction Steps

1-Bromobutane (0.92 ml, 8.512 mmol) in dry THF (5 ml) was slowly added to a stirred suspension of Mg metal (0.25 g, 10.059 mmol) and a catalytic amount of Iodine in dry THF (10 ml) at reflux temperature, and the reaction mixture stirred for 30 min after the completion of the addition. The prepared Grignard reagent was cooled to room temperature, then added dropwise over 15 min to a stirred solution of diethyl 2-(12-oxododecyl)malonate (2.65 g, 7.738 mmol) in THF (30 ml) at −10 to −15° C. and stirred at this temperature for 30 min. The reaction mixture was slowly warmed to room temperature and stirring continued for another one hour. The reaction was quenched with saturated ammonium chloride solution (10 ml), diluted with water (20 ml), extracted with diethyl ether (3×50 ml), dried on anhydrous MgSO4 and concentrated. The crude product was purified by silica gel column (4-6% EtOAc in hexane) and provided diethyl 2-(12-hydroxyhexadecyl)malonate (1.94 g, 62.5%) as a colorless liquid.

Provenance & Evidence