Benzeneacetonitrile, 4-bromo- → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 1617233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617233
[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([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOCC>[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 27914Benzeneacetonitrile, 4-bromo-HCID 516892Sodium BicarbonateHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (19.5 g), 2-(4-bromophenyl)acetonitrile (40 g), PdOAc2 (2 g), tetrabutylammonium bromide (40 g) and NaHCO3 (31.5 g) in THF (300 ml) was heated under N2 at reflux for 24 h. The mixture was cooled, diluted with ether (500 ml) and filtered through celite. The filtrate was washed with water, dried and evaporated under reduced pressure to give an oil, used crude in next step.

Aufarbeitung

  1. temperaturewas heated under N2
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-3d1bb5fd6f774048b1261d62463f46ae
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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