Hydrochloric Acid → 3-Hydroxy-2-(6-trifluoromethylpyridin-3-yl)-acrylic acid ethyl ester

HRID 1526079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526079
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOCC[O:21][CH2:20]1.C(OC=O)C.Cl>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:6]1[CH:7]=[N:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1)=[CH:20][OH:21])[CH3:2]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 59186932(6-Trifluoromethylpyridin-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 687048893-Hydroxy-2-(6-trifluoromethylpyridin-3-yl)-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.46 g (14.8 mmol) of the compound from Example 40A are initially introduced into 50 ml anhydrous toluene under argon, 712 mg (17.8 mmol) sodium hydride suspension (60% strength in paraffin oil) are added in portions and the mixture is stirred at RT for 1 h and then at 80° C. for 20 min. After cooling, 392 mg (1.48 mmol) 18-crown-6 and then, while cooling with ice, 2.20 g (29.7 mol) formic acid ethyl ester are added dropwise. The mixture is stirred first at 0° C. for 1 h and then at RT for 1 h. A mixture of 100 ml ethyl acetate and 150 ml 0.1 M hydrochloric acid is added, the phases are separated, the aqueous phase is extracted several times with ethyl acetate and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by means of flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient).

Aufarbeitung

  1. waitat 80° C. for 20 min
  2. temperatureAfter cooling
  3. additionare added dropwise
  4. stirringThe mixture is stirred first at 0° C. for 1 h
  5. waitat RT for 1 h
  6. additionis added
  7. customthe phases are separated
  8. extractionthe aqueous phase is extracted several times with ethyl acetate
  9. dry with materialthe combined organic phases are dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is purified by means of flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-1362ccd91a6a4f2792161f6d537a853f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085572B2

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