Heptane → HCID 90012346, compound

Participants

Reaction Conditions

Reaction Steps

A flask is charged with toluene (160 mL) and sodium bis(2-methoxyethoxy)aluminum dihydride (Red-Al, 137.9 g, 443.4 mmol, 65 wt. % in toluene). The solution is heated to 35° C. and treated with a solution of 2 (54.6 g, 369.5 mmol) in toluene (110 mL) at a rate sufficient to maintain the reaction temperature between 35-42° C. The reaction is stirred while cooling gradually at about 30° C. for 2 hours. The reaction is further cooled to 5° C. and quenched with ethyl acetate (10.3 mL) followed by 1.85N aqueous NaOH solution (176 mL), and the layers are separated. The organic phase is treated with a solution of sodium potassium tartrate (13.65 g) in water (112 mL), and the mixture is heated at 50° C. for about 15 minutes. After cooling at about 25° C., the layers are separated. The organic phase is washed with water (180 mL), and then concentrated by distillation under vacuum at about 50-55° C. to an oil. Toluene (30 mL) is added and the resultant solution is seeded with crystals of 3 (see below) and stirred at about 25° C. for 1 hour. At this point a thick slurry is obtained. Heptane (250 mL) is added dropwise over 30 minutes, stirred an additional 2 hours, and filtered. The solid is washed with heptane and dried under vacuum to provide 3 as a white solid. Yield: 30.4 g, 69.8% yield: Purity: 96.8 wt. %.

Provenance & Evidence