Hydrochloric Acid → HCID 70673606, Verbindung

HRID 341331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341331
[CH3:1][Si:2]([CH3:16])([CH3:15])[CH:3]=[CH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].CN(C)C(N(C)C)=N.Cl.[N+:26]([CH3:29])([O-:28])=[O:27]>>[N+:26]([CH2:29][CH:3]([Si:2]([CH3:15])([CH3:1])[CH3:16])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])([O-:28])=[O:27]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 86709898HCID 86709898, Verbindung

Produkt 1

HCID 70673606HCID 70673606, VerbindungAusbeute 88 %

Versuchsvorschrift

A solution of benzyl 3-(trimethylsilyl)acrylate (782 mg, 3.34 mmol) in nitromethane (3 ml)was added with N,N,N′,N′-tetramethylguanidine (105 μl, 0.838 mmol) at room temperature, and the mixture was stirred for 15 hours. The reaction mixture was added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)] to obtain benzyl 4-nitro-3-(trimethylsilyl)butanoate (863 mg, 88%) mentioned in the title as colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel chromatography [hexane/ethyl acetate (14:1)]

Quellen und Nachweise

ORD-Eintrag
ord-4c7ca60e07f74c8790f8d99f2d07ae4e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895769B2

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