Water → Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoate

HRID 280031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280031
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[CH3:9][O:10][C:11]1[CH:20]=[C:19]([CH:21]=O)[C:14]2[CH:15]=[CH:16][CH2:17][O:18][C:13]=2[C:12]=1[O:23][CH3:24].N1CCCCC1.O>C1C=CC=CC=1.C(O)(=O)C>[C:6]([C:5](=[CH:21][C:19]1[C:14]2[CH:15]=[CH:16][CH2:17][O:18][C:13]=2[C:12]([O:23][CH3:24])=[C:11]([O:10][CH3:9])[CH:20]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:8])#[N:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 128498327,8-Dimethoxy-5-formyl-2H-1-benzopyran

Produkt 1

HCID 54507081Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoateAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of ethylcyanoacetate (11.3 g, 0.1 mole), 7,8-dimethoxy-5-formyl-2H-1-benzopyran (22.0 g, 0.1 mole), piperidine (1.02 g, 0.01 mole) and acetic acid (0.36 g, 0.006 mole) in benzene (100 mL) was heated at reflux for 5 hr with azeotropic removal of water and allowed to cool. The solution was extracted successively with water (200 mL), 0.5N hydrochloric acid (200 mL), saturated sodium bicarbonate solution (200 mL), H2O (200 mL) and dried over magnesium sulfate. The volatiles were removed under reduced pressure to give 21.1 g (66.9%) of an orange solid, mp 104.5°-107.5° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto cool
  3. extractionThe solution was extracted successively with water (200 mL), 0.5N hydrochloric acid (200 mL), saturated sodium bicarbonate solution (200 mL), H2O (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe volatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dc96606c054d497e9f1c61ce46ffa255
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587342

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