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Hydrochloric Acid → 1-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one

HRID 1831883
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Reaktionsgleichung

Reaktionsgleichung von HRID 1831883
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:10][C:9]1=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 546786591-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one

Produkt 1

HCID 101495921-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133
Benzyl triethylammonium chloride
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one (10 mmol, 2.15 g), dichloromethane (100 mL), benzylbromide (11 mmol, 1.88 g), sodium hydroxide (2.5 N, 20 mmol, 8 mL), and benzyltriethylammonium chloride (0.5 g) were vigorously stirred at room temperature for 16 h. Hydrochloric acid (1 N) was added until the mixture produced an acidic reaction to pH paper. The mixture was then extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The product was obtained by flash chromatography eluting with ethyl acetate:hexanes (1:2). The appropriate fractions were concentrated to a clear oil. (1.3 g, 43%): 1H NMR (DMSO-d6/300 MHz) δ: 7.4-7.1 (m, 10H), 6.0-5.9 (m, 2H), 5.2 (s, 2H), 5.1 (s, 2H), 2.2 (s, 3H). ES HRMS m/z 306.147 (M+H, C20H19NO2 requires 306.149).

Aufarbeitung

  1. customproduced
  2. customan acidic reaction
  3. extractionThe mixture was then extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was obtained by flash chromatography
  9. washeluting with ethyl acetate:hexanes (1:2)
  10. concentrationThe appropriate fractions were concentrated to a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-8ab11c0724084fbeb547eff5c19b46a6
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07067540B2

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