1,2-Dichlorobenzene → HCID 86685136, compound

Participants

Reaction Steps

[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 5m (100 mg, 0.14 mmol) was dissolved in 5 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of o-dichlorobenzene (208 mg, 1.42 mmol) and Palladium/carbon (10 mg, 10%). The mixture was exchanged with H2 three times and stirred for 1.5 hours, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by thin layer chromatography with developing solvent system A to obtain the title compound (1S,2S,3S,4R,5S)-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 5 (58 mg, white solid), yield: 93.5%. MS m/z (ESI): 435.1 [M+1]; 1H NMR (400 MHz, CD3OD): δ 7.47 (d, 1H), 7.39-7.35 (m, 2H), 7.04 (s, 1H), 6.93 (d, 1H), 6.62 (d, 1H), 4.50 (t, 2H), 4.17 (d, 1H), 4.03 (s, 2H), 3.88-3.79 (m, 2H), 3.71-3.65 (m, 2H), 3.62-3.56 (m, 2H), 3.15 (t, 2H).

Provenance & Evidence