Beta-Nitrostyrene → HCID 59200437, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 1-iodo-2-((methoxymethoxy)methyl)benzene (4.51 g, 16.22 mmol) in THF (40 mL) under argon was added dropwise a solution of i-PrMgBr (9.5 mL, 2.12M in Et2O, 20.14 mmol) via syringe. The stirring was maintained at 0° C. After 1 hour, a solution of nitrostyrene (2.014 g, 13.50 mmol) in THF (40 mL) was added via cannula over 10 minutes and the stirring was maintained at 0° C. After 30 minutes, the reaction was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined extracts were dried (MgSO4), filtered and concentrated to an oil which was purified on Biotage Horizon (10-50% EtOAc:hexane, SiO2, 40+M) to afford the product (2.93 g) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.39 (m, 1H), 7.27-7.34 (m, 3H), 7.22-7.27 (m, 5H), 5.34 (t, J=8.08 Hz, 1H), 4.94-5.03 (m, 2H), 4.73 (d, J=11.87 Hz, 1H), 4.68 (q, J=6.57 Hz, 2H), 4.57 (d, J=11.87 Hz, 1H), 3.42 (s, 3H).

Provenance & Evidence