HCID 118377862, compound → HCID 131736391, compound

Participants

Reaction Steps

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehyde 23o (1.30 g, 1.75 mmol) in dry tetrahydrofuran (20 mL) was added dropwise methylmagnesium bromide (1.75 mL, 5.25 mmol, 3 M in ethyl ether) under N2 at 0° C. The mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (15 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=12/1 to give the title compound 23p as a white solid (0.48 g, 36%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CDCl3) δ(ppm): 7.38 (m, 11H), 7.22 (m, 5H), 6.93 (m, 2H), 6.66 (s, 1H), 6.53 (m, 1H), 4.99 (m, 1H), 4.94 (d, 1H), 4.80 (m, 2H), 4.31 (m, 2H), 4.04 (m, 5H), 3.95 (m, 2H), 3.83 (m, 2H), 3.70 (m, 1H), 1.45 (t, 3H), 1.28 (d, 3H).

Provenance & Evidence