Dimethyl Sulfide → HCID 69061372, compound

Participants

Reaction Steps

Into a cooled (−78° C.) solution of 3-cyano-N-(4-fluorobenzyl)-3-phenylhex-5-enamide (8.00 g, 24.8 mmol) in CH2Cl2 (500 mL) was bubbled ozone until a blue color persisted. The mixture was stirred for 10 min, then dimethyl sulfide (84.6 g, 1.36 mol) was added. After stirring for 48 hours at room temperature, the mixture was concentrated under vacuum. The residue was partitioned between EtOAc and water. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with 0-40% EtOAc in hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.45 (m, 5H), 7.29 (m, 2H), 7.15 (t, J=8.9 Hz, 2H), 6.78 (d, J=7.7 Hz, 1H), 5.50 (d, J=7.7 Hz, 1H), 4.72 (s, 2H), 3.17 (q, J=16 Hz, 2H) ppm. ES MS M+1=307.

Provenance & Evidence