1,2-Dichlorobenzene → HCID 117986015, compound

Participants

Reaction Steps

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 18c (156 mg, 0.20 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.11 mL, 0.99 mmol) and 10% Pd/C (21.0 mg, 0.02 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours under H2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/1 to give the title compound 18 as pale yellow oil (62.5 mg, 62.5%, HPLC: 95.60%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 563.3 [M+CHOO]−; and 1H NMR (600 MHz, DMSO-d6) δ(ppm): 7.43 (d, 1H), 7.39 (d, 1H), 7.33 (d, 1H), 7.15 (q, 2H), 6.97 (q, 2H), 4.70 (q, 2H), 4.02 (m, 3H), 3.80 (d, 1H), 3.70 (d, 1H), 3.45 (m, 2H), 1.20 (s, 3H), 1.15 (s, 3H).

Provenance & Evidence