1,2-Dichlorobenzene → HCID 117985965, compound

Participants

Reaction Steps

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 2c (155 mg, 0.21 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 5 mL) were added o-dichlorobenzene (155 mg, 1.06 mmol) and 10% Pd/C (22 mg, 0.02 mmol) in turn at room temperature. The mixture was stirred at room temperature under H2 for 1 hour and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/2 to give the title compound 2 as a white solid (90 mg, 91.8%, HPLC: 96.8%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 509[M+HCOO]−; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.35 (s, 2H), 7.30 (dd, 1H), 7.08 (d, 2H), 6.81 (d, 2H), 5.46 (t, 1H), 5.01 (d, 1H), 4.95 (d, 1H), 4.21 (s, 1H), 3.95 (d, 5H), 3.78 (d, 1H), 3.68 (dd, 1H), 3.43 (dd, 1H), 3.35 (m, 1H), 1.28 (t, 3H), 1.18 (s, 3H), 1.13 (s, 3H).

Provenance & Evidence