4-Chloro-3-hydroxybenzaldehyde → Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

HRID 1639889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639889
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[CH:12]/[CH:13]=[C:14](/[N:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)\[C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][C:42]=1[OH:49]>C(#N)C>[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([C:45]2[N:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][C:11]=2[C:4]2[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:43][C:42]=1[OH:49]

Komponenten

4

Edukt 2

HCID 138651144-Chloro-3-hydroxybenzaldehydeHCID 86637360ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate

Produkt 1

HCID 66720714Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylateAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Reflux a solution of 7.54 g (14 mmol) of ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate and 2.42 g (15.4 mmol) of 4-chloro-3-hydroxybenzaldehyde in 280 mL of anhydrous acetonitrile for 96 h. After cooling to RT, concentrate the reaction mixture under reduced pressure and purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc. After concentration under reduced pressure, we obtain 2.4 g of ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate in the form of white powder.

Aufarbeitung

  1. concentrationconcentrate the reaction mixture under reduced pressure
  2. custompurify the residue
  3. customobtained by silica gel column chromatography
  4. washeluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc
  5. concentrationAfter concentration under reduced pressure, we

Quellen und Nachweise

ORD-Eintrag
ord-0d06db0c8d324b92927a969ba8431a75
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110579B2

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