Tetrabutylammonium Fluoride → HCID 44815235, compound

Participants

Reaction Steps

A solution of 10 (20 mg, 0.086 mmol) in THF (0.6 mL) was degassed by gentle argon stream for 5 min. To the solution was added tetra-(n-butyl)ammonium fluoride (TBAF, 70 mg). The mixture was stirred at room temperature for 20 min. The mixture was diluted with methylene chloride/ether (1:2, 20 mL). The mixture was extracted with saturated aqueous sodium bicarbonate solution (10 mL×3). The basic extract was acidified with 5% aqueous HCl solution. The acidic mixture was extracted with methylene chloride/ether (1:2, 10 mL×4). The extract was washed with water (10 mL×2), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give a crystalline solid. The solid was purified by preparative TLC [hexanes-ethyl acetate (2.5:1)] to give MCE-3 as a crystalline solid (6.9 mg, 50%): 1H NMR (CDCl3) δ 7.39 (1H, d, J=1.8 Hz), 2.84 (1H, m), 2.62 (1H, m), 2.38 (1H, s), 2.32 (1H, m), 2.05 (1H, m), 1.55 (3H, s).

Provenance & Evidence