Acetic Acid → HCID 117985974, compound

Participants

Reaction Steps

To a solution of [(1R,2S,3S,4R,5S)-2,4-diacetoxy-1-(1-acetoxyethyl)-5-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-3-yl]acetate 31b (1.17 g, 1.98 mmol) in methanol (20 mL) was added sodium methoxide (85 mg, 1.57 mmol) at rt. The mixture was stirred at rt for 4 hours, and then acetic acid (0.1 mL) was added. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with EtOAc to give the title compound 31c as a white foam (0.78 g, 93.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, MeOD) δ(ppm): 7.44 (d, 1H), 7.42-7.34 (m, 2H), 7.03 (d, 2H), 6.70 (d, 2H), 4.17 (d, 1H), 4.06-3.98 (m, 3H), 3.92 (d, 1H), 3.78 (d, 1H), 3.66 (t, 1H), 3.55 (d, 1H), 1.33 (d, 3H).

Provenance & Evidence