Pyridine, hydrofluoride (1:1) → HCID 68815279, Verbindung

HRID 1436696Notizen

Reaktionsgleichung

[F:1][B-](F)(F)F.N#[O+].[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]2([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)SCCS2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1.C1C=CN=CC=1.[FH:41]>ClCCl>[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]([F:1])([F:41])[C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under nitrogen and in a plastic vessel, dissolve nitrosonium tetrafluoroborate (84.8 μg, 0.72 mmol) and pyridinium poly(hydrogen fluoride) (70% hydrogen fluoride, 30% pyridine, 300 μL) in dichloromethane (2 mL) and cool to 0° C. Add dropwise 5-(2-furan-2-yl-[1,3]dithiolan-2-yl)-N-methyl-N-propyl-isophthalamic acid methyl ester in dichloromethane (1.5 mL) to the mixture, warm up to room temperature and stir for 2 h. Dilute the mixture with dichloromethane (20 mL) and filter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture. Concentrate the filtrate and purify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes) to give the title compound (30%).

Aufarbeitung

temperaturewarm up to room temperature
filtrationfilter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture
concentrationConcentrate the filtrate
custompurify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-08e9fc8269834c689edf529d128ce798
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07618978B2

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