Sodium Iodide → HCID 20790071, compound

Participants

Reaction Conditions

Reaction Steps

Di(tert-butyl) malonate (151.4 g, 686 mmol) was added dropwise at 50° C. to a suspension of potassium tert-butylate (77 g, 686 mmol) in 500 ml of tert-butanol. Sodium iodide (10.33 g) was then added, followed by dropwise addition of Intermediate 5C (117.1 g, 686 mmol) at 40-50° C. The resulting thick suspension was stirred at 70° C. for two days. During this time, two further portions of potassium tert-butylate (15.4 g each, 70 mmol) were added. The mixture was then poured into ice-water and extracted three times with diethyl ether. The organic layers were dried over Na2SO4, filtered and evaporated. The crude product was finally purified by column chromatography using a cyclohexane/ethyl acetate gradient (70:1→15:1).

Provenance & Evidence