Sodium hydride → HCID 13878919, Verbindung

HRID 255455

Reaktionsgleichung

Reaktionsgleichung von HRID 255455
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.[N+:31]([C:34]([CH3:36])=[CH2:35])([O-:33])=[O:32]>C(#N)C.O1CCCC1>[N+:31]([CH:34]([CH3:36])[CH2:35][O:9][CH:3]1[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]1([CH3:10])[CH3:1])([O-:33])=[O:32]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 784862-Nitro-1-propeneHCID 5516962,2,5,5-Tetramethylcyclopentan-1-ol

Produkt 1

HCID 13878919HCID 13878919, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2,2,5,5-Tetramethyl-1-cyclopentanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sodium hydride (60% dispersion in oil) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6-ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of 2-nitropropene is added with vigorous stirring over a 10 minute period. After completion of the reaction as judged by thin layer chromatography, it is quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield 1-(2-nitropropoxy)-2,2,5,5-tetramethylcyclopentane.

Aufarbeitung

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with saturated ammonium chloride
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over MgSO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f06c1869e41f41c888d338b2f2c8b765
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698231

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