Triethylamine → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 445045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445045
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(#N)C.C1(C)C=CC=CC=1.O>[C:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:13]=1)#[N:19]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 27914Benzeneacetonitrile, 4-bromo-HCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Produkt 1

HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (70.0 g), 2-(4-bromophenyl)acetonitrile (126.5 g), PdCl2[P(o-tol)3]2 (4.2 g) and triethylamine (108.9 g) in acetonitrile (280 mL) was heated under nitrogen at 70° C. for 6 hours. The mixture was cooled to room temperature, diluted with toluene (840 mL) and water (840 mL) and stirred for 10 minutes. The organic layer was separated, washed with water (840 mL) and concentrated under reduced pressure to give the subtitle compound as a red oil, 158.7 g. This product was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water (840 mL)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a8d6376f78754e45938942e10dfc0e61
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476288B2

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