1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(tert-Butyl)-3,3-dimethyl-6-nitrobenzofuran-2(3H)-one

HRID 446141

Reaktionsgleichung

[C:1]([C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8](O)=[C:9]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C>C1COCC1>[C:1]([C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]2[O:14][C:12](=[O:13])[C:11]([CH3:16])([CH3:15])[C:9]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

To a solution of compound 18 (7.10 g, 25.2 mmol) in 710 mL of anhydrous THF was added EDCI (14.5 g, 75.6 mmol). The resulting suspension was left stirring at 30° C. overnight. The precipitate was filtered and thoroughly washed with DCM. The filtrate was concentrated to dryness and the residue was dissolved in DCM (100 mL). The solution was washed with water (50 mL×2) and brine (50 mL×1). The DCM layer was then dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified via column chromatography on silica gel (Petroleum ether/EtOAc 200:1→100:1→50:1) to give compound 19 as a white solid. 1H NMR (CDCl3; 400 MHz) δ 7.36 (s), δ 7.10 (s), δ 1.53 (s), δ 1.41 (s).

Aufarbeitung

waitThe resulting suspension was left
filtrationThe precipitate was filtered
washthoroughly washed with DCM
concentrationThe filtrate was concentrated to dryness
dissolutionthe residue was dissolved in DCM (100 mL)
washThe solution was washed with water (50 mL×2) and brine (50 mL×1)
dry with materialThe DCM layer was then dried over anhydrous Na2SO4
concentrationconcentrated
customto give the crude product, which
customwas purified via column chromatography on silica gel (Petroleum ether/EtOAc 200:1→100:1→50:1)

Quellen und Nachweise

ORD-Eintrag: ord-f1cbfc004dc74e56b8a9ebbb0701dcac
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08476442B2

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