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Acetaldehyde → 2,6-Difluoro-alpha-methyl-3-pyridinemethanol

HRID 16339
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16339
C(NC(C)C)(C)C.CCCCCC.C([Li])CCC.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1.[CH:27](=[O:29])[CH3:28].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[F:19][C:20]1[C:25]([CH:27]([OH:29])[CH3:28])=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 739342,6-DifluoropyridineHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 220383052,6-Difluoro-alpha-methyl-3-pyridinemethanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

In nitrogen atmosphere, diisopropylamine (134 mL) was dropwise added to a solution mixture of an n-butyl lithium hexane solution (2.62 M, 368 mL) and tetrahydrofuran (800 mL) at −60° C. or below. The resulting reaction solution was stirred at −60° C. for 30 min, and then a tetrahydrofuran solution (100 mL) of 2,6-difluoropyridine (100 g) was dropwise added thereto at −60° C. or below. The resulting reaction solution was stirred at the same temperature for 1 hr, and then acetoaldehyde (97.6 mL) was dropwise added thereto. Then, a 2 N hydrochloric acid aqueous solution (1000 mL) was dropwise added to the reaction solution, and further ethyl acetate (1000 mL) and toluene (1000 mL) were added thereto. The organic layer was separated and concentrated under reduced pressure to give 129 g of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. customThe resulting reaction solution
  2. customat −60° C. or below
  3. customThe resulting reaction solution
  4. stirringwas stirred at the same temperature for 1 hr
  5. additionwere added
  6. customThe organic layer was separated
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-491984727908469bba1e13abad271722
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737141B2

Notizen zur Reaktion

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