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Water → 6-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine

HRID 70718
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 70718
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][CH3:28])[N:21]=2)O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].O>ClCCCl.[Pd](Cl)Cl>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:20]2[N:21]=[C:22]([O:27][CH3:28])[C:23]([Cl:26])=[CH:24][CH:25]=2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 77195CyclopentanemethanolHCID 67396476(4-Tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol

Produkt 1

HCID 673980526-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium Chloride
Katalysator
HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Cyclopentylmethanol (0.039 mL) and palladium chloride (6.0 mg) were added to a solution of (4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol (110 mg) in 1,2-dichloroethane (2 mL) at room temperature, after which the mixture was stirred at 80° C. for six hours and then stirred at room temperature for two days. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 6-[(4-tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine as a pale red oil (112 mg, 86%).

Aufarbeitung

  1. stirringstirred at room temperature for two days
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-7f44cb7813bb4de49faaf82451fc6b10
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822503B2

Notizen zur Reaktion

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