Anisole → HCID 67482568, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) flask containing AlCl3 (622 mg, 4.66 mmol) was added a solution of the title compound of Example 12 Step C (674 mg, 1.17 mmol) and anisole (0.253 mL, 2.33 mmol) in toluene (3 mL). After 30 min, the mixture was removed from the 0° C. bath and allowed to stir at room temperature for 1.5 h, whereupon it was poured into H2O. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS E, tr=4.50 min, m/z 488.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.92 (s, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.29-7.25 (m, 2H), 7.23 (d, J=7.0 Hz, 2H), 7.20 (d, J=8.5 Hz, 2H), 7.08 (d, J=8.0 Hz, 2H), 6.86 (d, J=2.0 Hz, 1H), 3.86-3.81 (m, 1H), 3.85 (s, 3H), 3.20 (dd, J=14.0, 9.0 Hz, 1H), 3.13 (dd, J=14.0, 7.5 Hz, 1H), 2.92 (dd, J=13.5, 5.5 Hz, 1H), 2.83 (dd, J=13.5, 7.0 Hz, 1H), 1.23 (s, 9H).

Provenance & Evidence