Sodium hydride → 1-(2-Nitro-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

HRID 255460

Reaktionsgleichung

Reaktionsgleichung von HRID 255460
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].[CH2:13]1OCCOCCOCCOCCOCCOC1.[N+:31]([C:34]([CH3:36])=[CH2:35])([O-:33])=[O:32]>C(#N)C.O1CCCC1>[N+:31]([C:34]([CH3:13])([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 201657161-(2-Nitro-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

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 was 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 dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield 1-(2-nitro-2-methylpropoxy)-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 dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a03652a6ebeb4c5e9fb1539dca7e83d1
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698231

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