Citric Acid → HCID 178487492, Verbindung

HRID 392579

Reaktionsgleichung

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16]C.[CH:19]([C:21]1[N:22]=[CH:23][N:24](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:25]=1)=[O:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCCCCC>[NH:24]1[CH:25]=[C:21]([C:19]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[CH:3]=2)([OH:20])[CH:15]([CH3:16])[CH3:14])[N:22]=[CH:23]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

2-Bromo-6-methoxynaphthalene (30 g) was dissolved in THF (400 ml) and cooled to −78° C. A solution (1.6 M; 99 ml) of n-butyl lithium in hexane was added dropwise, and the mixture was stirred at −78° C. for 30 min. A solution (300 ml) of 4-formyl-1-trityl-1H-imidazol (38.9 g) in THF was slowly added dropwise. After stirring at −78° C. for 30 min, the reaction mixture was poured into 3% aqueous citric acid solution (600 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer was combined and the mixture was washed with saturated brine, dried and concentrated. The residue was washed with ethyl acetate to give the title compound (35.0 g) as a colorless solid.

Aufarbeitung

stirringAfter stirring at −78° C. for 30 min
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washthe mixture was washed with saturated brine
customdried
concentrationconcentrated
washThe residue was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-20e5d771f14d45b690271d4c31551114
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06800778B1

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