6-Methoxypyridine-3-carbaldehyde → Ethyl 3-(6-methoxy-3-pyridyl)acrylate

HRID 224881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 224881
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12]C([O-])=O>N1CCCCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:12][C:11]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Produkt 1

HCID 53930754Ethyl 3-(6-methoxy-3-pyridyl)acrylateAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 6-methoxypyridine-3-carboxaldehyde (2.34 g), monoethyl malonate (4.51 g), pyridine (12 ml) and piperidine (6 drops) was heated under reflux for 5 hours and was evaporated to an oil. This oil was partitioned between ether and dilute aqueous ammonia. The ether layer was washed with water and evaporated to an oil which crystallised on standing to give ethyl 3-(6-methoxy-3-pyridyl)acrylate (2.8 g, 79%) m.p. 49°-52°.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customwas evaporated to an oil
  4. customThis oil was partitioned between ether and dilute aqueous ammonia
  5. washThe ether layer was washed with water
  6. customevaporated to an oil which
  7. customcrystallised

Quellen und Nachweise

ORD-Eintrag
ord-82b636fa743a4d50919b942bcbffa88e
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234588

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