Hydrochloric Acid → HCID 24851307, compound

Participants

Reaction Steps

A solution of 1-(4-hydroxyphenyl)-3-phenylpropenone 3 (9 mmol) in EtOH (15 mL) was treated with diethylamine (4.6 mL, 45 mmol) and nitromethane (4.8 mL, 90 mmol) and heated under reflux for 16 h. The solution was cooled and acidified with 4 M HCl, partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was stirred in cold Et2O (30 mL) for 10 min and filtered to give the product 4 as a colorless solid (1.84 g, 73%), m.p. 112-113° C. (MeOH). 1H NMR (300 MHz, CDCl3): δ 7.86 (d, J=8.5 Hz, 2H), 7.35-7.26 (m, 5H), 6.85 (d, J=8.5, 2H), 5.44 (s, 1H), 4.86-4.80 (m, 1H), 4.64-4.71 (m, 1H), 4.25-4.16 (m, 1H), 3.46-3.31 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 195.3, 160.3, 139.2, 130.6, 129.6, 129.0, 127.8, 127.4, 115.4, 79.6, 41.1, 39.4. IR (KBr disc): 3427, 1646 cm−1. ES-MS: m/z 284.1 [M−H]− HRMS [M+Na]+: 308.0887, C16H15NNaO4+ requires 308.0899.

Provenance & Evidence