Tetrahydrofuran → 3-(4-Nitro-thiophen-2-ylmethylene)-3H-isobenzofuran-1-one

HRID 600268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600268
COP([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])NN=1)(=O)OC.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=O)[S:24][CH:25]=1)([O-:20])=[O:19].C(N(CC)CC)C.C1C[O:38]CC1>O>[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7](=[O:38])[O:17]2)[S:24][CH:25]=1)([O-:20])=[O:19]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8188574-Nitrothiophene-2-carbaldehydeHCID 86628633HCID 86628633, Verbindung

Produkt 1

HCID 689101193-(4-Nitro-thiophen-2-ylmethylene)-3H-isobenzofuran-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (4-oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester (3.85 g, 15.9 mmol) in THF (30 mL) was added 4-nitro-thiophene-2-carbaldehyde (25) (2.5 g, 15.9 mmol) under nitrogen. Triethylamine (2.2 mL 15.9 mmol) was added dropwise over 10 minutes and then stirred at room temperature for 4 hours. The yellow suspension was poured in water (80 mL), and the then filtered, the solid was washed with water (15 mL), hexane (10 mL) and then diethyl ether (10 mL) and then dried in vacuo to afford a 4.1 g of the desired products. Two peaks in LC-MS analysis, (4.1 g, 94%) and required no further purification; m/z (LC-MS, ESP), RT=4.71 mins (M+H) 274, & RT=4.84 mins (M+H) 274;

Aufarbeitung

  1. filtrationthe then filtered
  2. washthe solid was washed with water (15 mL), hexane (10 mL)
  3. dry with materialdiethyl ether (10 mL) and then dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4d90028aa22a4d56ac086b9fbf7ce389
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902193B2

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