Trifluoroacetic acid → HCID 86679662, Verbindung

HRID 577720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577720
[CH:1]1(/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.[CH2:18]([N:25]([CH2:31]O)[CH2:26][Si](C)(C)C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH2:18]([N:25]1[CH2:31][C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 11040780ethyl (2E)-3-cyclopropylacrylate2×HCID 70869782HCID 70869782, Verbindung

Produkt 1

HCID 86679662HCID 86679662, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl (2E)-3-cyclopropylacrylate (5.3 g, 37.9 mmol) and TFA (0.43 g, 3.79 mmol) in DCM (100 mL) was added dropwise {benzyl[(trimethylsilyl)methyl]amino}methanol (13.5 g, 56.8 mmol) at 0° C. After the addition, the mixture was refluxed overnight. TLC (petroleum ether: EtOAc 10:1) indicated most of ethyl (2E)-3-cyclopropylacrylate was consumed. The reaction mixture was quenched with sat. NaHCO3 (100 mL), brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether: EtOAc=50:1 to 30:1) to give the title compound (5.8 g, 54% yield) as a yellow oil.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed overnight
  3. customwas consumed
  4. customThe reaction mixture was quenched with sat. NaHCO3 (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether: EtOAc=50:1 to 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-5b0e6e18759340e187af8d1108b4b065
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040547B2

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