Gamma-Butyrolactone → 3-Benzyloxolan-2-one

HRID 1383959

Reaktionsgleichung

Reaktionsgleichung von HRID 1383959
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14]1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1>[CH2:19]([CH:14]1[CH2:15][CH2:16][O:17][C:13]1=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 5

HCID 7302Gamma-ButyrolactoneHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 178418339Butyllithium

Produkt 1

HCID 5627583-Benzyloxolan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of diisopropylamine (15.18 g, 0.15 mol) in dry tetrahydrofuran (200 ml) at −78° C. under a nitrogen atmosphere, n-butyllithium (1.6 M in hexanes, 94 ml, 0.15 mol) was added dropwise. After twenty minutes of stirring at −78° C., γ-butyrolactone (12.91 g, 0.15 mol) was added dropwise, such that the reaction temperature was maintained below −70° C. After twenty minutes of stirring at −78° C., a mixture of benzyl bromide (25.65 g, 0.15 mol) and hexamethylphosphoramide (26.85 g, 0.15 mol) was added dropwise to the reaction mixture. The reaction mixture was then permitted to warm to −30° C. and stirred at this temperature for two hours.

Aufarbeitung

  1. temperaturewas maintained below −70° C
  2. stirringAfter twenty minutes of stirring at −78° C.
  3. additionwas added dropwise to the reaction mixture
  4. temperatureto warm to −30° C.
  5. stirringstirred at this temperature for two hours

Quellen und Nachweise

ORD-Eintrag
ord-afb7fdb87bf34c0ea54d6fa6461a9e24
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255494B1

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