Water → HCID 89963253, Verbindung

HRID 337880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337880
[H-].[Na+].[C@H:3]12[O:9][C@H:8]1[CH2:7][CH2:6][CH2:5][C@H:4]2[OH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:19]>C1COCC1>[CH2:11]([O:10][C@:4]1([OH:19])[CH2:5][CH2:6][CH2:7][C@H:8]2[C@H:3]1[O:9]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 330105AC1L766H

Produkt 1

HCID 89963253HCID 89963253, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of sodium hydride (63%; 1.20 g, 31.5 mmol) in THF (20 mL), a solution of the (1R*,2R*,6S*)-7-oxabicyclo[4.1.0]heptan-2-ol (3.10 g, 27.2 mmol) prepared in Example 100a in THF (20 mL) was added with cooling on ice, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, benzyl bromide (4.0 mL, 33.4 mmol) was added, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1) to yield the title compound (2.85 g, 51%) as a light brown oil.

Aufarbeitung

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-16e1b8293e0647809ce88222feb558d7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889741B2

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