Triethylamine → 3-(4-methoxy-3-nitrobenzylidene)-3H-isobenzofuran-1-one

HRID 459778

Reaktionsgleichung

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28].C(N(CC)CC)C>O1CCCC1>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[O:3]2)=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: 15 °C

Versuchsvorschrift

A stirred solution of dimethyl 3-oxo-1,3,-dihydroisobenzofuran-1-ylphosphonate (2.42 g, 0.01 mol; prepared in a manner similar to that described in Example 23) and 4-methoxy-3-nitrobenzaldehyde (1.81 g, 0.01 mol) in tetrahydrofuran (15 ml) was cooled to 15° C. and a solution of triethylamine (1.01 g, 0.01 mol) in tetrahydrofuran (1.5 ml) was added dropwise at <25° C. The mixture was stirred at ambient temperature for 4 hours, allowed to stand at this temperature for a further 16 hours and the resulting mixture was concentrated in vacuo. The residue was triturated with water (50 ml) and stirred at ambient temperature for 2 hours before the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(4-methoxy-3-nitrobenzylidene)-3H-isobenzofuran-1-one (2.53 g) as a yellow solid, m.pt. 173–181° C., which was used directly in the next stage.

Aufarbeitung

customprepared in a manner similar to
waitto stand at this temperature for a further 16 hours
concentrationthe resulting mixture was concentrated in vacuo
customThe residue was triturated with water (50 ml)
stirringstirred at ambient temperature for 2 hours before the resulting solid
filtrationwas collected by filtration
customdried in vacuo for 24 hours

Quellen und Nachweise

ORD-Eintrag: ord-57d87a8d33454567be00b86794b82fc6
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07196085B2

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