Phenethylamine → Methyl 4-(phenylethylamino)crotonate

HRID 365638

Reaktionsgleichung

Reaktionsgleichung von HRID 365638
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].Br[CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20]>C1COCC1>[C:3]1([CH2:2][CH2:1][NH:9][CH2:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Produkt 1

HCID 23291030Methyl 4-(phenylethylamino)crotonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of phenethylamine (20 mL, 160 mmol) in anhydrous THF (250 mL) was added NaHCO3 (7 g) followed by methyl 4-bromocrotonate (10 mL, 84 mmol). After stirring for 4 h the reaction was concentrated to approximately half the volume and filtered through a pad of silica gel and eluted with 2% MeOH/CHCl3 to wash off the product. The crude product obtained after evaporation of the filtrate was purified by flash chromatography (silica gel, 2% MeOH/CHCl3) to give the title compound as a slightly yellow liquid (16.5 g, 81%). TLC Rf 0.53 (5% MeOH/CHCl3); 1H NMR (CDCl3) δ 1.2 (1H, s), 2.8 (4H, br s), 3.35 (2H, dd), 3.7 (3H, s), 5.95 (1H, dt), 7.0 (1H, dt), 7.25 (5H, br s)

Aufarbeitung

  1. concentrationwas concentrated to approximately half the volume
  2. filtrationfiltered through a pad of silica gel
  3. washeluted with 2% MeOH/CHCl3
  4. washto wash off the product
  5. customThe crude product obtained
  6. customafter evaporation of the filtrate
  7. customwas purified by flash chromatography (silica gel, 2% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-148325671f5a49eaa1b8b4a6389e5e11
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127359

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