Acetic Acid → HCID 58264995, compound

Participants

Reaction Steps

Prepared according to general procedure A using tert-butyl 3-(2-hydroxy-4-methyphenyl)-3-oxopropanoate (250 mg, 1.0 mmol), benzaldehyde (100 μL, 1.00 mmol), 12.0 mL benzene, piperidine (10 μL, 0.10 mmol) and glacial acetic acid (5.7 μL, 0.10 mmol), refluxed for 3 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 154 mg (46%) of white solid. mp=92-95° C.; IR (film) 2977.9; 1718.2; 1627.9; 1155.0 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.95 (bs, 1H), 7.82 (s, 1H), 7.40 (d, J=9.6 Hz, 1H), 7.36-7.29 (m, 5H), 6.83 (s, 1H), 6.61 (d, J=8.0 Hz, 1H), 2.34 (s, 3H), 1.41 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 200.8, 163.9, 163.0, 149.0, 142.0, 133.0, 131.8, 131.7, 130.6, 130.3, 129.1, 120.9, 118.5, 118.0, 82.7, 28.1, 22.3; LRMS (electrospray): Mass calculated for C21H22O4 [M]+, 338.15. Found [M+23]+, 361.2. An NOE difference experiment was conducted for this compound and a positive NOE was seen for the alkene proton when the tert-butyl signal was irradiated and a positive NOE was seen for the tert-butyl signal upon irradiation of the alkene proton.

Provenance & Evidence