Dimethylformamide → HCID 86651666, compound

Participants

Reaction Conditions

Reaction Steps

To a THF (0.06 M) solution of 8-bromo-6-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)quinoline (1 eq.) was added at −78° C. n-butyl lithium (2.5 M in hexane, 2.1 eq.) dropwise over a period of 10 min. The resulting yellow solution was stirred at −78° C. for 15 min before DMF (2 eq.) was added dropwise over a period of 10 min. The now red solution was stirred at −78° C. for another 2 h before the reaction mixture was quenched with the addition of sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil that solidified upon standing.

Provenance & Evidence