HCID 86590984, compound → HCID 69599637, compound

Participants

Reaction Steps

Bis(tricyclohexylphosphine)benzylidene ruthenium dichloride (0.11 g, 0.1289 mmol) was weighed directly into a 50 mL flask, placed under a N2 atmosphere, and dry CH2Cl2 (10 mL) was added, followed by a solution of 6g (1.1020 g, 2.5778 mmol) in dry CH2Cl2 (15 mL). The purple reaction mixture was refluxed for 3 h, an additional 0.11 of catalyst was added, and refluxing was continued for another 2 hours. The mixture was then allowed to cool to room temperature and filtered through a short, densely-packed pad of Silica Gel 60H for thin layer chromatography (φ˜3.8 cm, 1˜2 cm), which was washed with CH2Cl2 (5×20 mL). Evaporation gave a brown oil which was purified via column chromatography (5% EtOAc-hexanes→30% EtOAc-hexanes) to afford 0.500 g (50% yield) of 7g as a brown oil. 1H NMR (400 MHz) in CDCl3 (J, Hz): δ 4.3375 (ddd, 1H, NOCHH), 4.6139 (ddd, 1H, NOCHH), 6.0447 (dt, 1H, NOCH2CH═CH), 6.3715 (s, 1H, NCH), 6.7020 (dt, 1H, NOCH2CH), 6.9626 (s, 1H, CHPh2), 7.10-7.40 (m, 15H, ArH). MS (CI, isobutane), m/z: 400 (M++1).

Provenance & Evidence