Methyl Acrylate → Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoate

HRID 592812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592812
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>N12CCN(CC1)CC2.C(Cl)(Cl)Cl>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10](=[CH2:11])[C:9]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 2

HCID 7294Methyl AcrylateHCID 142732-Pyridinecarboxaldehyde

Produkt 1

HCID 11008779Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9237DabcoKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A 250-mL single-neck round-bottomed flask was charged with chloroform (100 mL), picolinaldehyde (10.7 g, 0.10 mol), methyl acrylate (8.60 g, 0.10 mol), and 1,4-diaza-bicyclo[2.2.2]octane (0.560 g, 5.00 mmol). The reaction mixture stirred at room temperature for 48 h. After this time the reaction was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 193a as dark yellow oil (11.6 g, 60%). MS-ESI: (M+H)+ 194.2. 1H NMR (500 MHz, CDCl3) δ 8.54 (d, J=5.0 Hz, 1H), 7.69-7.66 (m, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.22-7.20 (m, 1H), 6.36 (s, 1H), 5.97 (s, 1H), 5.62 (s, 1H), 4.85 (s, 1H), 3.74 (s, 3H).

Aufarbeitung

  1. concentrationAfter this time the reaction was concentrated under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with 3:1 petroleum ether/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cda74360b64842e4ba48f40e475c8cd0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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