Oxazole → HCID 68816107, Verbindung

HRID 732492

Reaktionsgleichung

C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25](I)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1>C1COCC1.C(OCC)C.[Cl-].[Zn+2].[Cl-].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25]([C:7]2[O:6][CH:10]=[CH:9][N:8]=2)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Add n-butyllithium (1.6 M in hexanes, 1.25 mL, 2.01 mmol) dropwise to a solution of oxazole (126 mg, 1.83 mmol) in THF (12.6 mL) at −78° C. Stir for 30 min at −78° C. and add a solution of zinc chloride (747 mg, 5.49 mmol) in diethyl ether (5.5 mL) and stir at 0° C. for 1 h. Add a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid methyl ester (330 mg, 0.91 mmol) in THF (5.1 mL) followed by tetrakis(triphenylphosphine)palladium (0) (105 mg, 0.091 mmol) and heat to reflux for 30 min. Add ethyl acetate (40 mL), wash with water (2×20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexane) to give the title compound (225 mg, 82%).

Aufarbeitung

stirringstir at 0° C. for 1 h
temperatureheat
temperatureto reflux for 30 min
washAdd ethyl acetate (40 mL), wash with water (2×20 mL)
dry with materialdry (magnesium sulfate)
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag: ord-212d4cacf3a84ebda025b0d1763030c4
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07585885B2

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