Boron trifluoride etherate → HCID 86725309, compound

Participants

Reaction Conditions

Reaction Steps

The product from step (a) was dissolved in DCM (20 ml) and cooled to 0° C. To the stirred solution triethylsilane (943 μL, 5.85 mmol) was added, followed by borontrifluoride etherate (456 μL, 3.66 mmol). After 1 hour, additional borontrifluoride etherate (456 μL, 3.66 mmol) was added and the reaction mixture was stirred for an additional hour at 0° C. The reaction was quenched with saturated aqueous NaHCO3 (50 ml) and the aqueous layer was extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo. The residue was purified by silica gel chromatography (gradient elution: 0 to 20% EtOAc in hexane) to give the sub-title compound as a colorless oil (103 mg). 1H NMR (CDCl3) δ 7.01-6.93 (m, 2H); 4.16 (q, J=7.2 Hz, 2H); 3.75-3.68 (m, 2H); 3.52-3.43 (m, 2H); 3.11-2.99 (m, 4H); 2.80-2.72 (m, 2H); 2.25-2.14 (m, 1H); 2.06-1.99 (m, 1H); 1.29 (t, J=6.9 Hz, 3H); 0.88-0.77 (m, 1H); 0.55-0.41 (m, 2H); 0.34-0.26 (m, 1H); 0.20-0.13 (m, 1H); MS: ESI (positive): 300, (M+1).

Provenance & Evidence