Hydrochloric Acid → HCID 23371775, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of step e (7.60 g) in dry tetrahydrofuran (30 ml) is added over 15 min. to a stirred mixture of magnesium turnings (0.85 g) and iodine (0.06 g) in dry tetrahydrofuran (25 ml) at 45° C. under an argon atmosphere. The mixture is heated under reflux for 3 h, cooled to 5° C., treated with bis-(triphenylphosphine)nickel (II) chloride (0.32 g) and a solution of 4-bromopicoline (4.8 g) in dry tetrahydrofuran (50 ml) and stirred at room temperature for 18 h. The mixture is treated with HCl (140 ml, 1M) and extracted with diethyl ether (2×60 ml). The combined ether extracts are washed with HCl . The combined acid solutions are basified to pH 10 with K2CO3, extracted with diethyl ether (3×100 ml), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product. This is purified by chromatography (silica gel, 10% acetone in hexane) to give the title compound as an oil, having the following physical characteristics: 1H-NMR(δ-CDCl3): 1.44 (s,6H), 2.21 (s,3H), 2.59 (s, 3H), 5.60 (d,1H), 6.31 (d,1H), 6.70 (s,1H), 6.82 (s,1H), 7.04 (dd,1H), 7.09 (d,1H) and 8.49 (d,1H).

Provenance & Evidence