Dimethylformamide → HCID 66670107, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere a solution containing 69 (5.92 g, 10.1 mmol) in anhydrous DMF (50 mL) was charged with (n-Bu)4NCl (2.8 g, 10.1 mmol), K2CO3 (1.4 g, 10.1 mmol), NaHCO2 (0.68 g, 10.1 mmol), and Pd(OAc)2 (0.045 g, 0.20 mmol) at ambient temperature. The heterogeneous mixture was immersed in a pre-heated (85° C.) oil bath. After 3 h, TLC analysis revealed some 69 remained therefore additional catalyst (0.01 g) was added. After an additional 1 h of heating, 69 was completely consumed by TLC analysis [1:1 EtOAc/hexanes, Rf(69) 0.3; Rf(70)=0.8]. The warm reaction mixture was cooled in an ice bath then diluted with diethyl ether and filtered through a pad of celite. The solids were washed with diethyl ether and the filtrate was washed several times with water to remove excess DMF, then washed once with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 5.1 g of crude 70 which was purified by flash silica gel chromatography (20% EtOAc/hexanes) to afford 3.0 g (59%) of 70 as a white solid. 1H NMR (CDCl3, 300 MHz) δ5.18 (m, 1H), 7.60 (m, 1H), 7.18 (m, 1H), 7.05 (dt, J=2.4, 8.7 Hz, 1H), 4.13 (m, 1H), 3.41 (m, 1H), 3.33 (m, 2H), 3.17 (app dd, J=14.1, 38.1 Hz, 1H), 2.61 (s, 3H), 1.83 (m, 3H), 1.69 (m, 1H), 1.49 (s, 94) ppm.

Provenance & Evidence