Dimethylformamide dimethyl acetal → HCID 86662869, Verbindung

HRID 1483810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483810
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1.CCN(C(C)C)C(C)C.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[CH3:29][N:27]([CH3:28])[CH:26]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:13])[F:14])[CH:5]=1)[C:11]#[N:12]

Komponenten

4

Edukt 3

HCID 78373Dimethylformamide dimethyl acetalHCID 81531DiisopropylethylamineHCID 5179063-(Trifluoromethoxy)phenylacetonitrile

Produkt 1

HCID 86662869HCID 86662869, VerbindungAusbeute 72 %

Versuchsvorschrift

A mixture of 3-trifluoromethoxyphenylacetonitrile (2.5 grams, 12.43 mmol), DIPEA (0.321 grams, 2.48 mmol), and dimethyl formamide dimethyl acetal (20 mL) were heated at reflux for 4 h. On cooling, the reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution. The aqueous phase was extracted with ethyl acetate and the combined organic phase washed with brine and concentrated in vacuo. The crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams) to give pure product (2.3 grams, 8.98 mmol, 72% yield.).

Aufarbeitung

  1. temperaturewere heated
  2. temperatureat reflux for 4 h
  3. temperatureOn cooling
  4. customthe reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phase washed with brine
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams)
  9. customto give pure product (2.3 grams, 8.98 mmol, 72% yield.)

Quellen und Nachweise

ORD-Eintrag
ord-7e11d1d1871f4df89f203fb5a3b65e82
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416132B2

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