Triethylamine → 1-Chloro-4-{1-[(E)-2-nitroethenyl]cyclobutyl}benzene

HRID 331690

Reaktionsgleichung

Reaktionsgleichung von HRID 331690
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12](O)[CH2:13][N+:14]([O-:16])=[O:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(/[CH:12]=[CH:13]/[N+:14]([O-:16])=[O:15])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66747669HCID 66747669, Verbindung

Produkt 1

HCID 667468521-Chloro-4-{1-[(E)-2-nitroethenyl]cyclobutyl}benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(1-(4-Chlorophenyl)cyclobutyl)-2-nitroethanol (5.2 g, 20.34 mmol) was dissolved in dichloromethane (41 ml) and trifluoroacetic acid anhydride (2.87 ml, 20.34 mmol) was added. The reaction mixture was cooled to 0° C. and triethylamine (5.67 ml, 40.7 mmol) was added dropwise. The reaction was slowly warmed to room temperature and stirring Was continued for 2 h. The reaction mixture was diluted with dichloromethane and washed with aqueous hydrochloric acid (1 N). The organic layer was dried (magnesium sulfate) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 3.99 g (16.79 mmol, 83%)

Aufarbeitung

  1. temperatureThe reaction was slowly warmed to room temperature
  2. washwashed with aqueous hydrochloric acid (1 N)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Quellen und Nachweise

ORD-Eintrag
ord-0d12ee125a564d98892a285f8e239deb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877794B2

Verknüpfte Notizen

Wird geladen…