1-Bromohexane → HCID 18537656, compound

Participants

Reaction Steps

To a suspension of sodium hydride (1.26 g 55% w/w) in anhydrous N,N-dimethylformamide (100 ml) was added t-butyl N-[5-(4-t-butoxycarbonylaminophenoxy)-2-nitrophenyl]-N-methylcarbamate (12.1 g). The mixture was stirred at room temperature for several minutes. To this mixture was added hexyl bromide (6.5 g) in an ice bath and the mixture was stirred for 30 minutes and then at room temperature for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using toluene:diisopropyl ether=100:7 as the eluant to afford the desired compound (13.8 g). Rf=0.32: thin layer chromatography on a silica gel plate using toluene/diisopropyl ether=100:7 as the eluant.

Provenance & Evidence