Boron Trichloride → HCID 86693881, compound

Participants

Reaction Steps

A solution of compound 26 (1.38 g, 2.6 mmol) in anhydrous CH2Cl2 was treated with boron trichloride (7.1 ml, 1M solution in CH2Cl2, 8.1 mmol) at −78° C. during 15 minute. After stirred at the same temperature for another 15 min, additional portion of boron trichloride (5.1 mL of 1M solution in CH2Cl2) was added. The reaction was quenched with MeOH at −78° C. after 15 min and concentrated under reduced pressure. The residue was purified by column chromatography on the silica gel (EtOAc:Hexane=1;10 to 1:3) to give 27 (0.84 g, 78%). [α]24D−53.55° (c 0.5, MeOH); 1H NMR (500 MHz, CDCl3) δ 4.65 (dt, J=8.0 & 15.0 Hz, 1H), 4.49-4.45 (m, 1H), 4.26-4.21 (m, 1H), 3.99 (dd, J=4.5 & 12.0 Hz, 1H), 3.89 (dd, J=6.0 & 11.5 Hz, 1H), 2.66 (s, 1H), 0.93-1.08 (m, 28H), 0.72 (m, 1H), 0.68-0.43 (m, 2H), 0.28 (m, 1H); 19F NMR (500 MHz, CDCl3) δ −195.8 (m); 13C NMR (125 MHz, CDCl3) δ 7.8, 12.5, 12.7, 13.3, 13.4, 16.9, 16.98, 17.07, 17.08, 17.4, 17.5, 27.5 29.8, 49.1, 63.7, 73.7, 74.7, 102.3 (d, J=192.7 Hz); HR-MS Calcd. For (C20H39FO4Si2+H)+ 418.2592. found 418.2592.

Provenance & Evidence