Acetonitrile → HCID 86590510, compound

Participants

Reaction Steps

A solution of EXAMPLE 65A (4.07 g) and oxalyl chloride (1.82 mL) in dichloromethane (80 mL) was treated with N,N-dimethylformamide (0.0459 mL), stirred for 2 hours, concentrated, and dissolved in dichloromethane (30 mL) to provide an acid chloride solution. A suspension of the potassium salt of diethyl malonate (8.41 g) in acetonitrile (80 mL) at 0° C. was treated with magnesium chloride (6.58 g) and triethylamine (6.88 mL), warmed to ambient temperature, stirred for three hours, treated with the acid chloride solution, stirred for 1 hour, and concentrated. The concentrate was treated with 1M HCl (100 mL) and extracted with ethyl acetate. The extract was washed with 1M HCl, saturated sodium bicarbonate and brine, dried (MgSO4), filtered, and concentrated; and the concentrate was flash chromatographed on silica gel with 25% ethyl acetate/hexanes.

Provenance & Evidence