Dimethylformamide → HCID 21706869, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 6-bromo-2-t-butyloxynaphthalene (2.00 g, 7.16 mmol) in dry THF (30 mL) under nitrogen was added 2.5 m n-butyl lithium in hexanes (3.16 mL, 7.88 mmol). The resulting solution was stirred 0.5 hours at −78° C. and dry DMF (1.66 mL, 21.56 mL) was added neat. The cooling bath was removed, the reaction was allowed to stir for 1 h, and quenched with excess saturated ammonium chloride. The reaction was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. Purification on silica gel with 10% ethyl acetate/hexanes gave the title compound (1.47 g, 90%) as a colorless oil. mp 51-52° C.;

Provenance & Evidence