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Water → 3,5-Dihydroxymethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine

HRID 129934
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 129934
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([C:22](OCC)=[O:23])=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2].O>C1(C)C=CC=CC=1.O1CCCC1>[OH:11][CH2:10][C:9]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][C:6]([CH:27]([CH3:28])[CH3:29])=[C:7]([CH2:22][OH:23])[C:8]=1[C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 962WaterHCID 10179180Diethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylate

Produkt 1

HCID 159242263,5-Dihydroxymethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

22.8 ml (80 mmol) of a 3.5 molar solution of sodium bis-(2-methoxyethoxy)-dihydroaluminate in toluene are added under nitrogen to a solution of 4.6 g (11.4 mmol) of the compound from Example 3 in 100 ml of dry tetrahydrofuran at -10° C. to -5° C. The mixture is stirred overnight at room temperature and then warmed to 40° C. for 5 h. After cooling again to 0° C., 100 ml of water are cautiously added dropwise and the mixture is extracted three times using 100 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether (6:4)).

Aufarbeitung

  1. temperaturewarmed to 40° C. for 5 h
  2. temperatureAfter cooling again to 0° C.
  3. extractionthe mixture is extracted three times
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether (6:4))

Quellen und Nachweise

ORD-Eintrag
ord-807464af99064c0188a9d890aa837aa1
Quelldatensatz
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05470982

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