Hydrochloric Acid → HCID 67015643, Verbindung

HRID 1617503

Reaktionsgleichung

Reaktionsgleichung von HRID 1617503
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:14]#[N:15])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[CH3:2].[C:17]1([CH3:25])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Mg]Cl.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:14]#[N:15])[CH:6]([C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH3:25])[CH3:2]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178424304HCID 178424304, Verbindung

Produkt 1

HCID 67015643HCID 67015643, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (6.65 g) in toluene (50 mL) was added to a solution of o-tolylmagnesium chloride in THF (1M, 30.9) at 0° C. After the addition was complete, the solution was heated to 85° C. for 1.5 hours, and stirring was continued at rt overnight. The mixture was heated for additional 2 hours to 85° C., cooled and poured onto ice. 1M HCl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (Et2O/n-heptane 1:3) to yield the title compound (6.45 g, 73%) as a light yellow oil, MS (ESI−): m/z=370.0444 ([M−H]−, 1Br).

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe mixture was heated for additional 2 hours to 85° C.
  3. temperaturecooled
  4. additionpoured onto ice
  5. customthe phases were separated
  6. extractionthe inorganic one was extracted with EtOAc (2×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by flash chromatography on silica gel (Et2O/n-heptane 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-0351cf0fc309490b92fc09579787351f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765730B2

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