Methallyltrimethylsilane → HCID 68794579, compound

Participants

Reaction Steps

To a mixture of methallyltrimethylsilane (185 μL, 1.05 mmol) and 23 (0.28 g, 0.35 mmol) in anhydrous methylene chloride (10 mL) at −20° C. was added BF3 OEt2 (88 μL, 0.70 mmol) in a drop-wise manner. The resulting light orange mixture was stirred for 1 hour, during which the temperature was allowed to rise to 0° C. The reaction mixture was quenched with 10% NaHCO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered, and evaporated to yield a residue which was purified by column chromatography eluting with 0-15% EtOAc in petroleum ether to give 24 (153 mg, 52%). 1H NMR (300 MHz, CDCl3) δ 7.18-7.30 (m, 20H), 7.00-7.05 (m, 1H), 6.98 (s, 4H), 6.69 (s, 1H), 4.67 (t, J=10.8 Hz, 1H), 4.49-4.60 (m, 8H), 4.24 (d, J=11.4 Hz, 1H), 4.12 (d, J=6.0 Hz, 1H), 3.67-4.00 (m, 7H), 3.54 (s, 3H), 3.07 (d, J=16.2 Hz, 1H), 2.79 (d, J=15.9 Hz, 1H), 2.55 (q, J=7.5 Hz, 2H), 1.54 (s, 3H), 1.17 (t, J=7.5 Hz, 3H). LC/MS m/z 860 (M+Na).

Provenance & Evidence