Water → HCID 14248988, Verbindung

HRID 18027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18027
[CH3:1][C:2]([CH:6]1[O:10][O:9][C:7]1=[O:8])([CH2:4]O)[CH3:3].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1.ClCCl>[CH2:13]([O:10][C@@H:6]1[C:2]([CH3:1])([CH3:3])[CH2:4][O:9][C:7]1=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22244486D(-)-Pantolactone

Produkt 1

HCID 14248988HCID 14248988, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of D(−)-pantolactone (20.0 g, 153.7 mmol) and sodium hydride (4.4 g, 184.4 mmol) in anhydrous THF was stirred under an atmosphere of nitrogen at room temperature for 1 hour. The resultant mixture was treated with benzyl bromide (31.5 g, 184.4 mmol) and stirred at room temperature overnight. The product mixture was treated with water and diluted with dichloromethane. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to purification on silica gel eluting with 0-5% methanol in dichloromethane gradient. Collection and concentration of appropriate fractions provided the title compound.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was subjected to purification on silica gel eluting with 0-5% methanol in dichloromethane gradient
  8. customCollection and concentration of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-523dccc1c3b84241ab3e653878ebd506
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741315B2

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