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Sodium Hydroxide → (3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methanol

HRID 31577
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 31577
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][C:16]2([CH2:21][CH2:22][CH3:23])[O:20][CH2:19][CH2:18][O:17]2)[CH:9]=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>CO>[CH3:12][C:11]1[C:6]([CH2:5][OH:4])=[N:7][CH:8]=[CH:9][C:10]=1[O:13][CH2:14][CH2:15][C:16]1([CH2:21][CH2:22][CH3:23])[O:20][CH2:19][CH2:18][O:17]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59792410(3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl acetate

Produkt 1

HCID 59792407(3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methanolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The (3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl acetate (1.19 g, 3.68 mmol) obtained in the step (3d) was mixed with a 1N aqueous sodium hydroxide solution (5 ml) and methanol (10 ml). The mixture was stirred at room temperature for 3 hours and concentrated under reduced pressure. The residue was suspended in tetrahydrofuran and sodium sulfate was added to the suspension, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in a solution mixture containing heptane and ethyl acetate at a ratio of 2:1 and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=2/1) to obtain the title compound (0.88 g, 85%) as a colorless oil.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionsodium sulfate was added to the suspension
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in a solution mixture
  6. additioncontaining heptane and ethyl acetate at a ratio of 2:1
  7. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-0dd8fd1d24ae4fbca4c0a7efb65ca574
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07425634B2

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