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Magnesium Bromide → HCID 118194622, Verbindung

HRID 529292
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 529292
[CH:1]1([CH2:5][CH:6]=[N:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.[Mg+2].[Br-].[Br-].C[Si](C)(C)[O:20][C:21]([O:29][CH2:30][CH3:31])=[C:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:8]([NH:7][CH:6]([CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[C:22]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[C:21]([O:29][CH2:30][CH3:31])=[O:20])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 82241Magnesium BromideHCID 12614350Trimethyl[(1,2,2-triethoxyethenyl)oxy]silaneHCID 21867204Cyclohexane ethylacetateHCID 118201132HCID 118201132, Verbindung

Produkt 1

HCID 118194622HCID 118194622, VerbindungAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

N-(2-cyclobutylethylidene)-1-phenylmethanamine (1.00 g, 5.3 mmol) was dissolved in 23 mL toluene, MgBr2.0Et2 (2.07 g, 8.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Trimethyl(1,2,2-triethoxyvinyloxy)silane (1.83 g, 7.4 mmol) was added, and the mixture was stirred at room temperature. After 3 hours, the reaction was quenched with water (30 mL) and acidified to pH=2 with hydrochloric acid. The organic phase was washed with sat. NaHCO3, dried over Na2SO4 and the solvent was removed under vacuum to yield the crude product. Column chromatography (silica, cyclohexane:ethyl acetate 10:1) yielded 1.1 g ethyl 3-(benzylamino)-4-cyclobutyl-2,2-diethoxybutanoate.

Aufarbeitung

  1. addition0Et2 (2.07 g, 8.0 mmol) was added
  2. stirringthe mixture was stirred at room temperature
  3. waitAfter 3 hours
  4. customthe reaction was quenched with water (30 mL)
  5. washThe organic phase was washed with sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed under vacuum
  8. customto yield the crude product

Quellen und Nachweise

ORD-Eintrag
ord-48ebae4860504e72a7cd92e8ed05a9c3
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346853B2

Notizen zur Reaktion

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