Trifluoroacetic acid → HCID 68898935, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diethyl 2-(3-methoxy-2-nitrobenzylidene)malonate, which was prepared from 3-methoxy-2-nitrobenzaldehyde following the procedure described in Example 1, Part C (162 mg, 0.5 mmol) in 10 mL of methylene chloride was added added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (237 mg, 1.0 mmol) and trifluoroacetic acid (0.010 mL, 0.125 mmol). The solution was allowed to stir at 40° C. for 18 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (elution with 4:1 hexane/EtOAc) to afford 201 mg (88%) of the title compound. 1H NMR (CDCl3): δ 7.40-7.25 (m, 7H), 6.93-6.85 (m, 1H), 4.36-4.30 (m, 1H), 4.32-4.15 (m, 2H), 3.87 (s, 3H), 3.77 (q, 2H), 3.69 (s, 2H), 3.60-3.50 (m, 1H), 3.05-2.97 (m, 1H), 2.85-2.78 (m, 1H), 2.75-2.68 (m, 1H), 1.23 (t, 3H, J=7.2 Hz), 0.83 (t, 3H, J=7.2 Hz). LRMS (ESI): 457.4 (M+H)+.

Provenance & Evidence