Potassium Carbonate → HCID 10689805, compound

Participants

Reaction Steps

DMF (5 mL) at r.t. was added to a stirring mixture of 4-hydroxy-3,5-dimethylbenzaldehyde (116 mg, 0.78 mmol), potassium carbonate (214 mg, 1.55 mmol) and a-methyl-2-nitro-4,5-dimethoxybenzyl bromide (169 mg, 0.58 mmol) and stirring was continued for 44 hours. The reaction was diluted with 5% NaHCO3 (100 mL) and aqueous workup (Et2O, MgSO4) followed by concentration in vacuo yielded a yellow oil which was purified by flash chromatography (20 g, 5:1 hexanes/ethyl acetate) to yield 7e (125 mg, 60%) as a yellow oil: 1H NMR (270 MHz, CDCl3) d 1.56 (d, J=6.2 Hz, 3H), 2.22 (s, 6H), 3.92 (s, 3H), 4.01 (s, 3H), 5.83 (q, J=6.2 Hz, 1H), 7.49 s, 3H), 7.57 (s, 1H), 9.81 (s, 1H); 13C NMR (68 MHz, CDCI3) d 17.6, 23.5, 56.4, 56.5, 76.6, 107.5, 109.0, 131.1, 131.7, 132.1, 134.5, 139.0, 148.1, 153.8, 160.5, 191.5.

Provenance & Evidence