Iodine → HCID 67127506, compound

Participants

Reaction Steps

A catalytic amount of iodine was added to magnesium (5.1 g) in 50 ml diethyl ether. After 10 minutes a solution of 2-bromothiophene (5.7 g) in 10 ml THF was added to this reaction mixture. Once the Grignard reaction had started, 2-bromothiophene (15 ml) dissolved in 50 ml THF was added dropwise and on completion of the addition the mixture was stirred for two hours at room temperature. 8-Azetidin-1-yl-1,4-dioxaspiro[4,5]decane-8-carbonitrile (12 g) dissolved in 60 ml THF was added dropwise to this reaction mixture at 60-70° C. under a nitrogen atmosphere. Then the reaction mixture was stirred for 1 hour at room temperature and the reaction progress was monitored by thin-layer chromatography (50% EtOAc/hexane). Once the conversion was complete the reaction mixture was cooled to 0° C., quenched with saturated ammonium chloride solution (50 ml) and then extracted with ethyl acetate (2×100 ml). The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica, 5-10% EtOAc/hexane). The desired product was obtained as a brown solid (10.2 g, 68%).

Provenance & Evidence