Iodine → N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide

Participants

Reaction Conditions

Reaction Steps

Magnesium powder (0.548 g, 22.6 mmol) was placed into a round-bottomed flask with a small piece of iodine. Dry THF was added to cover the magnesium and the solution was heated to a gentle reflux until the color had dissipated (approximately 30 minutes). While refluxing, a second solution of 4-bromo-1-buten (2.3 mL, 22.6 mmol) in dry THF (5 mL) was added. After 12 min, the mixture was cooled 0° C. and added to a solution of 3-(4-chlorobenzyl)-3-formamido-N-methoxy-N-methylcyclobutanecarboxamide (0.5 g, 1.61 mmol) in dry THF (30 mL). After 2 h, the reaction was allowed to warm to room temperature and stir overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with diethyl ether (×2). The combined organic layers were washed successively with 1M HCl, water and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated to give the crude product (0.48 g) that was used to the next step without further purification. ESI MS found for C17H20ClNO2 m/z [306.3 (M+1), 328.3 (M+Na+), 304.5 (M−1)].

Provenance & Evidence