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

HRID 519387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519387
[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-diazabicyclo[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 127a as a 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-9800804356534564994625b31eaf3070
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115152B2

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