Isophorone → HCID 10612307, compound

Participants

Reaction Steps

This compound was prepared from isophorone (2.065 g, 14.94 mmol) and p-nitrobenzyl bromide (4.06 g, 18.80 mmol, 1.25 equiv) in the manner previously described for the synthesis of enone 13, affording 1.891 g (46%), of the nitro-enone as a pale yellow oil. 1H NMR (400MHz, CDCl3) δ0.98 and 1.13 (2s, 2×3H, geminal-CH3 's), 1.92 (s, 3H, 3-CH3), 2.17 and 2.31 (ABq, 2H, JAB =18.5 Hz, 4-H), 2.38 (dd, 1H, J=9.0, 3.3 Hz, 6-H), 2.75 and 3.05 (d of ABq, 2H, JAB =14.0 Hz, JA =3.2 Hz, JB =8.9 Hz, benzylic-CH2), 5.84 (s, 1H), 7.33 (d, 2H, J=8.2 Hz, Ar--H) and 7.53 ppm (d, 2H, J=8.2 Hz, Ar--H).

Provenance & Evidence