Water → HCID 23147093, Verbindung

HRID 495299

Reaktionsgleichung

Reaktionsgleichung von HRID 495299
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([C:11]2[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][C:16]([O:23][CH2:24][O:25][CH3:26])=[CH:15][C:12]=2[CH:13]=[O:14])=[CH:8][CH:7]=1.[CH2:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)C.C1([Li])C=CC=CC=1.O>C(OCC)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([C:11]2[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][C:16]([O:23][CH2:24][O:25][CH3:26])=[CH:15][C:12]=2[CH:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[OH:14])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 21895417Cyclohexane diethyletherHCID 23147566HCID 23147566, VerbindungHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 23147093HCID 23147093, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-[5-(1,3-Dioxolan-2-yl)furan-2-yl]-3,5-bis(methoxymethoxy)benzaldehyde (135 mg, 0.374 mmol) was dissolved in diethyl ether (10 mL), and the solution was cooled to −78° C., and then cyclohexane/diethyl ether solution of 1.06 mol/L phenyllithium (0.54 mL, 0.57 mmol) was added thereto and stirred at the same temperature for 1 hour. Water was added to the reaction mixture, and extracted with diethyl ether. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was extracted out under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (chloroform/methanol=50/1) to obtain 1-{2-[5-(1,3-dioxolan-2-yl)furan-2-yl]-3,5-bis(methoxymethoxy)phenyl}-1-phenylmethanol (93.9 mg, 57%).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. extractionthe solvent was extracted out under reduced pressure
  5. customThe resulting residue was purified through preparative thin-layer chromatography (chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-3e6800d13ea44c318885fbc99d4c9651
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538241B2

Verknüpfte Notizen

Wird geladen…