Boron Trichloride → HCID 10738692, compound

Participants

Reaction Steps

A solution of 14b (0.324 g, 0.685 mmol) in CH2Cl2 (20 mL) was cooled to -78° C., treated with boron trichloride (1.0M in dichloromethane, 2.74 mL, 2.74 mmol), and stirred for 1 h at that temperature. The reaction mixture was quenched with saturated NaHCO3 solution (3.0 mL), and immediately partitioned between chloroform and a pH 7 buffer solution. The organic layer was washed with water, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography over silica gel with EtOAc/hexane (1:1) as eluant to give 14c (0.252 g, 96%) as a white solid: mp 48° C.; IR (KBr) 3489 (OH), 1735 (C=O) and 1667 cm-1 (C=C); 1H NMR (CDCl3) δ 0.86 (distorted t, 3 H, CH3), 1.10-1.50 (m, 22 H, >C=CHCH2 (CH2)11CH3), 2.08 (s, 3 H, CH3CO), 2.60-2.90 (m, 2 H, >C=CHCH2), 3.59 (AB m, 2 H, CH2OH), 4.18 (2 AB multiplets, 4 H, H-5, CH2OAc), 6.28 (t, 1 H, J=7.6 Hz, 1 H, >C=CH); 13C NMR (CDCl3) δ 14.11, 20.72, 22.68, 27.61, 29.06, 29.24, 29.35, 29.41, 29.55, 29.64, 31.91, 47.58, 64.42, 65.34, 69.86, 126.06, 147.72, 169.69, 171.19; FAB MS m/z 383 (MH+, 100). Anal. Calcd for C22H38O5 : C, 69.07; H, 10.01. Found: C, 69.06; H: 10.03.

Provenance & Evidence