Acetic Acid → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 445051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445051
[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(O)(=O)C>C(#N)C.C1(C)C=CC=CC=1>[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 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27914Benzeneacetonitrile, 4-bromo-HCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (30.0 g, 0.23 mol), 2-(4-bromophenyl)acetonitrile (54.2 g, 0.28 mol), PdCl2[P(o-tol)3]2 (1.8 g, 2 mmol) and triethylamine (46.7 g, 0.46 mol) in acetonitrile (90 g) was heated at 70° C. for 6 hours under a N2 atmosphere. The mixture was cooled to 25° C., diluted with toluene (300 g) and 10% aq. acetic acid (360 g), and stirred for 10 minutes. The organic layer was separated, washed with water (360 g), and concentrated under reduced pressure to give the subtitle compound as a red oil, 67.3 g. This product was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled to 25° C.
  2. customThe organic layer was separated
  3. washwashed with water (360 g)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ff1ea654c3f24d7ab597a834cff93c9c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476288B2

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