Heptane → HCID 178491130, compound

Participants

Reaction Steps

A solution of Example 1G (3.236 kg) and para-anisaldehyde (1.484 kg) in toluene (6.631 kg) was heated at 80° C. for 2 hours, treated with heptane (33.147 kg) over 50 minutes, cooled to room temperature over 20 hours, and filtered. The filter cake was rinsed with heptane (6.994 kg), air dried, then vacuum dried (100 mmHg) at 50° C. to provide 4.297 kg (97.6%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.35 (s, 1H), 7.73 (dt, 2H, J=8.9, 2.9 Hz), 7.61 (dt, 2H, J=8.8, 2.9 Hz), 7.41 (dd, 2H, J=8.9, 1.1 Hz), 7.05 (dt, 2H, J=8.8, 2.9 Hz), 7.01 (dt, 2H, J=8.8, 2.9 Hz), 4.87 (br s, 1H), 4.31 (dd, 1H, J=9.9, 4.1 Hz), 4.13 (dd, 1H, J=9.9, 7.4 Hz), 3.81 (s, 3H), 3.64-3.80 (m, 2H), 3.56 (dd, 1H, J=10.0, 6.3 Hz).

Provenance & Evidence