Boron Trichloride → HCID 131736382, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(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]-3-trimethylsilyl-prop-2-yn-1-ol 4a (0.65 g, 0.81 mmol) in dichloromethane (30 mL) was added dropwise boron trichloride (8.89 mL, 8.89 mmol, 1 M in dichloromethane) at −78° C. The mixture was stirred at −78° C. for 2 hours. After the addition, the reaction mixture was quenched with 5 mL of water and adjusted to pH 6-7 with saturated aqueous sodium hydrogen carbonate. The resulting mixture was extracted with dichloromethane (30 mL×3). The combined organic layers were washed with water (20 mL×2) and then saturated aqueous sodium chloride (20 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound 4b as red oil (0.43 g, 100%). The crude product was used in next step without further purification. The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.40 (m, 1H), 7.29 (m, 1H), 7.10 (d, 2H), 6.82 (d, 2H), 4.69 (t, 1H), 4.23 (m, 1H), 4.12 (m, 1H), 4.10 (m, 1H), 4.02 (m, 2H), 3.99 (m, 1H), 3.75 (d, 1H), 3.71 (d, 1H), 2.71 (d, 1H), 2.65 (d, 1H), 1.42 (t, 3H), 0.21 (s, 9H).

Provenance & Evidence