Benzene → 2-(4-tert-Butoxycarbonyl-2-nitro-benzylidene)-succinic Acid Dimethyl Ester

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (13.3 g, 50.7 mmol) and dimethyl maleate (7.31 g, 50.7 mmol) were combined in glacial acetic acid (62 mL) at 25° C. and stirred for 6 h whereupon benzene (164 mL) and 4-formyl-3-nitro-benzoic acid tert-butyl ester (8.5 g, 33.8 mmol) was added. The dark solution was heated at reflux for 18 h then cooled to 25° C. Concentration in vacuo gave a dark oil. Flash chromatography (silica gel, hexane/ethyl acetate) affords the title compound as an amber oil (11.1 g, 87%). NMR (dmso-d6, 300 MHz) : δ1.6 (s, 9H, tert-butyl), 3.3 (s, 2H, CH2), 3.6 (s, 3H, CH3), 3.8 (s, 3H, CH3), 7.5-8.6 (m, 4H, ArH, ArCH).

Provenance & Evidence