Cyclohexanecarboxaldehyde → HCID 16125893, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to general procedure B using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (236 mg, 1.0 mmol), cyclohexanecarboxaldehyde (120 μL, 1.0 mmol) 7.0 mL benzene, piperidinium acetate (2.0 mL, 0.025M in toluene) and sodium sulfate (2.1 g), stirred at 22° C. for 8 d. Purified via column chromatography with 5% EtOAc/hexanes, yielding 165 mg (50%) of a white solid. Rf=0.59 (10% ether/hexanes); mp=62-65° C.; IR (film) 2929.2; 1716.6; 1631.9; 1257.5; 1153.6 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.92 (s, 1H); 7.51-7.46 (m, 2H); 7.02 (d, J=8.2 Hz, 1H); 6.90-6.86 (m, 2H); 2.11 (m, 1H); 1.68-1.60 (m, 5H); 1.35 (s, 9H); 1.20-1.15 (m, 5H). 13C NMR (125 MHz, CDCl3) δ 200.8, 163.7, 162.6, 152.2, 136.9, 132.3, 124.6, 120.5, 119.2, 118.4, 82.3, 31.9, 28.5, 28.0, 25.8, 25.1; LRMS (electrospray): Mass calculated for C20H26O4 [M]+, 330.18. Found [M+23]+, 353.6.

Provenance & Evidence