1-Iodododecane → HCID 86613070, compound

Participants

Reaction Steps

Sodium hydride (3.60 g, 60%, 90.0 mmol) was washed with pentane (3×) before DMF (150 ml) and (+)-(2R,3R)-2,3-dihydroxy-N,N,N′,N′-tetramethylsuccinamide (9.2 g, 45.0 mmol, origin: Aldrich) were added. The reaction mixture was left stirring at room temperature for 90 min, then a solution of 1-iodododecane (28.0 g, 94.5 mmol) in DMF (50 ml) was added. The reaction was left stirring for another 2 h at room temperature and then heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was extracted with ether (4×), washed with water (2×), dried (Na2SO4), and concentrated. Column chromatography (SiO2, dichloromethane/acetone 3:1) gave 5.93 g (28%) of a pale-yellow solid.

Provenance & Evidence