Hydrochloric Acid → HCID 123280337, compound

Participants

Reaction Steps

The mixture of 12 (1.53 g, 5.68 mmol), Pd2(dba)3 (260 mg, 5% mmol), P(t-Bu)3 (0.23 mL, 1 M in toluene, 4% mmol) in dry toluene (30 mL) was stirred under N2 protection for 15 min. Then a solution of LHMDS in toluene (6.2 mL, 1 M in toluene, 6.2 mmol) was added dropwise. After stirred at ambient temperature overnight, the resultant dark color suspension was added 1 N hydrochloric acid (8 mL) slowly. The resulting mixture was stirred at ambient temperature for 2 hours. Then the suspension was filtered through celite and the filtrate was diluted with dichloromethane (70 mL). The organic layer was washed with saturated NaHCO3 aqueous solution, brine, and dried over Na2SO4. After filtered and concentrated, the crude product was purified by silica gel column using hexane and ethyl acetate (2:1) as eluent to give 1.03 g light yellow solid, in 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, J=15.9 Hz, 1H), 7.35 (d, J=8.48 Hz, 2H), 6.65 (d, J=8.56 Hz, 2H), 6.22 (d, J=15.9 Hz, 1H), 5.12 (seq, J=6.24 Hz, 1H), 3.91 (brs, 2H), 1.30 (d, J=6.24 Hz, 6H); 13C NMR (100 MHz, CDCl3): δ 167.20, 148.56, 144.55, 129.80, 124.88, 114.84, 114.35, 67.32, 22.00. mp 78-80° C. IR v (Diamond, cm−1): 3417, 3335, 1673, 1592, 1513, 1264, 1168, 1104, 980, 823. MS (ESI) m/z found 206.2 (M+H)+.

Provenance & Evidence