Water → HCID 56925649, compound

Participants

Reaction Steps

To a solution of 23 (200 mg, 0.83 mmol) in anhydrous THF (5 mL) at −78° C. was added BuLi (2.5M, 0.35 mL) and stirred for 35 minutes, then DMF (0.08 mL, 0.1 mmol) was added dropwise. The reaction was stirred at −78° C. for 30 additional minutes. Water (3 mL) was added to quench the reaction and was extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography; 20:1 Hx/EtOAc. To give the product as a yellowish solid (23% yield). 1H NMR δ 1.53 (s, 6H), 6.01 (d 1H, J=10.4), 6.58 (d, 1H, J=10.4), 7.13 (d, 1H, J=8.4), 7.77 (d, 1H, J=8.4), 9.93 ppm (s, 1H). 13C NMR δ 28.8, 78.7, 123.0, 123.3, 123.4, 136.3, 145.8, 153.7, 191.9 ppm

Provenance & Evidence