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

HRID 2302004Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:28][CH3:29])(=[O:27])/[CH:21]=[CH:22]\[C:23]([O:25][CH3:26])=[O:24].C1C=CC=CC=1.[C:36]([O:40][C:41](=[O:53])[C:42]1[CH:47]=[CH:46][C:45]([CH:48]=O)=[C:44]([N+:50]([O-:52])=[O:51])[CH:43]=1)([CH3:39])([CH3:38])[CH3:37]>C(O)(=O)C.CCCCCC.C(OCC)(=O)C>[CH3:26][O:25][C:23](=[O:24])[C:22](=[CH:48][C:45]1[CH:46]=[CH:47][C:42]([C:41]([O:40][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:53])=[CH:43][C:44]=1[N+:50]([O-:52])=[O:51])[CH2:21][C:20]([O:28][CH3:29])=[O:27]

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

additionwas added
temperatureThe dark solution was heated
temperatureat reflux for 18 h
concentrationConcentration in vacuo
customgave a dark oil

Sources & evidence

ORD record: ord-09d2abc5ccf14805b2c374c47b799620
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06429214B1

Reaction notes

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