HCID 19601773, compound → HCID 19601769, compound

Participants

Reaction Steps

To 50.0 mg (0.17 mmol) of alcohol 15 in 4 ml of MeOH was added 2 drops of concentrated HCl. The mixture was heated at reflux for 5 min, cooled to RT, quenched with water, and the products extracted with ether. The ether layer was washed (water then brine), dried (MgSO4), filtered and concentrated. Purification by preparative TLC (SiO2, 5% EtOAc-95% hexanes) gave 33.0 mg (0.12 mmol) of 1-[3-t-butyl-5-(1-phenyl-vinyl)-phenyl]-ethanone 16 (71% yield). Rf 0.8; 1H-NMR (CDCl3) δ 1.34 (s, 9H, 3CH3), 2.58 (s, 3H, COCH3), 5.48 (s, 1H,CH=), 5.55 (s, 1H, CH=), 7.34 (m, 5H, Ar--H), 7.56 (t, J=3.7 Hz, 1H, Ar--H), 7.72 (t, J=3.7 Hz, 1H, Ar--H), 7.96 (t, J=3.7 Hz, 1H, Ar--H).

Provenance & Evidence