Dimethyl Sulfide → HCID 57672469, compound

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of (2S,3R,Z)-methyl 3-(4-(benzyloxy)phenyl)-2-methylhex-4-enoate 41.2 (0.45 g, 1.4 mmol), trichloroborane (0.99 g, 8.5 mmol) and dimethylsulfane (0.53 g, 8.5 mmol) in DCM (10.0 mL) was stirred at 0° C. for 5 minutes and then at room temperature for 7 hours. A saturated solution of sodium bicarbonate was added slowly at 0° C. to reach a pH of 6.5. EtOAc was added, and the organic layer was washed with brine (2×25 mL) and dried with Na2SO4. The product was purified by reverse phase HPLC to give the title compound (41.3) as the major product in a ratio of 95:5. 1H NMR (500 MHz, CDCl3) δ ppm 1.21 (d, J=6.85 Hz, 3H) 2.77 (td, J=6.97, 2.93 Hz, 1H) 3.47-3.50 (m, 3H) 3.82 (m, 1H) 5.50-5.65 (m, 2H) 6.71-6.80 (m, 2H) 7.08 (d, J=8.56 Hz, 2H). MS ESI (pos.) m/e: 235.1 (M+H)+.

Provenance & Evidence