(3-Bromophenyl)acetonitrile → Methyl 2-(3-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 1617241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617241
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:12]=[C:13]([CH2:17][C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1.C([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[C:18]([CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])#[N:19]

Komponenten

6

Edukt 3

HCID 36023(3-Bromophenyl)acetonitrileHCID 516892Sodium BicarbonateHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Produkt 1

HCID 68414943Methyl 2-(3-(cyanomethyl)benzyl)-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (11.37 ml), 2-(3-bromophenyl)acetonitrile (22 g) PdOAc2 (3.15 g), tetrabutylammonium bromide (30.1 g) and NaHCO3 (19.64 g) in THF (40 ml) was heated at reflux for 24 h. The mixture was partitioned between ether and water, the organics separated, washed with water, dried and evaporated under reduced pressure to give the subtitle compound, 22 g.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was partitioned between ether and water
  4. washthe organics separated, washed with water
  5. customdried
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ab4b018e123840dfbb8c355585409967
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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