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Dichloromethane → 3-(2-Methoxy-pyridin-4-yl)-propionic acid methyl ester

HRID 705996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 705996
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH3:13])[CH:7]=1.C(Cl)Cl>[Pd].CCO>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH3:13])[CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6344DichloromethaneHCID 677751253-(2-Methoxy-pyridin-4-yl)-acrylic acid methyl ester

Produkt 1

HCID 142234703-(2-Methoxy-pyridin-4-yl)-propionic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 3-(2-methoxy-pyridin-4-yl)-acrylic acid methyl ester (1.3 g, 6.72 mmol, 1 eq) and Pd/C, 10% (357 mg, 0.05 eq, 10%) was stirred in a DCM (15 ml)/absolute EtOH (15 ml) solvent mixture under hydrogen atmosphere for 1 hour at room temperature. Palladium was filtered off over a celite pad, the solvent was evaporated and obtained crude was purified by chromatography on BIOTAGE SP1 purification device using 25 g normal phase silica SNAP coloumn and cyclohexane/EtOAc solvent system (gradient 3-30% of EtOAc in 20 coloumn volumes). Solvent from the gathered fractions of appropriate composition was evaporated and obtained was 3-(2-methoxy-pyridin-4-yl)-propionic acid methyl ester (1.22 g, yield=88.2%, purity=95%) in form of transparent colourless oil. MS: [M+H]+=196.14 1H NMR (300 MHz; CDCl3) δ/ppm 2.63 (t, J=7.91 Hz, 2H), 2.90 (t, J=7.91 Hz, 2H), 3.68 (s, 3H), 3.92 (s, 3H), 6.57 (s, 1H), 6.72 (dd, J=5.33 Hz, J=1.29 Hz, 1H), 8.06 (d, J=5.33 Hz, 1H)

Aufarbeitung

  1. filtrationPalladium was filtered off over a celite pad
  2. customthe solvent was evaporated
  3. customobtained crude
  4. customwas purified by chromatography on BIOTAGE SP1 purification device
  5. customSolvent from the gathered fractions of appropriate composition was evaporated
  6. customobtained

Quellen und Nachweise

ORD-Eintrag
ord-efa6a6d5e0d94c999ec821584ea368da
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174968B2

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