Sodium Methoxide → 3-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-dimethoxymethylpropanenitrile

HRID 280030

Reaktionsgleichung

Reaktionsgleichung von HRID 280030
[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]=[C:17]([CH2:20][O:21][CH3:22])[C:18]#[N:19])[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:23][CH3:24]>CO.O>[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH2:16][CH:17]([CH:20]([O:2][CH3:1])[O:21][CH3:22])[C:18]#[N:19])[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:23][CH3:24]

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 543734473-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile

Produkt 1

HCID 201297603-(7,8-Dimethoxy-2H-1-benzopyran-5-yl)-2-dimethoxymethylpropanenitrileAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of sodium methoxide (8.86 g, 0.164 mole), and 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (Example 37A, 23.1 g, 0.080 mole) in methanol (60 mL) was heated at reflux for 24 hr, allowed to cool and diluted with water (200 mL). The resultant mixture was extracted with toluene (1×200 mL and 2×100 mL). The combined toluene portions were extracted with water (3×100 mL) and dried over magnesium sulfate. The toluene solution was concentrated leaving a brown oil which was distilled under reduced pressure to give 15.9 g (62%) of a yellow oil which was used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureto cool
  4. extractionThe resultant mixture was extracted with toluene (1×200 mL and 2×100 mL)
  5. extractionThe combined toluene portions were extracted with water (3×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe toluene solution was concentrated
  8. customleaving a brown oil which
  9. distillationwas distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b37f6d563f0f43dea23f939cc7c3bba2
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587342

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