Tetrahydrofuran → HCID 57705499, Verbindung

HRID 1662412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662412
[CH3:1][C:2]([Si:5]([CH3:30])([CH3:29])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:9]=1)([CH3:4])[CH3:3].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[CH3:4][C:2]([Si:5]([CH3:29])([CH3:30])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23]([OH:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:9]=1)([CH3:1])[CH3:3]

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706379HCID 57706379, Verbindung

Produkt 1

HCID 57705499HCID 57705499, VerbindungAusbeute 80 %

Versuchsvorschrift

To a stirred solution of 66.30A (0.500 g, 1.2 mmol) in THF (15.00 mL, 183 mmol) at 0° C. was added LAH in THF (2.3 mL, 2.3 mmol, 1.0M). The reaction was stirred for two hours. 1N NaOH(aq) was added to quench the reaction mixture, and the reaction was then extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.30B as a colorless oil (0.400 g, 80% yield).

Aufarbeitung

  1. customto quench the reaction mixture
  2. extractionthe reaction was then extracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d3ca36ddca474aefbf9febfd27df7790
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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