Methanol → Methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate

HRID 218351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218351
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20].CO>C(OCC)(=O)C>[CH3:18][N:19]([CH3:21])/[CH:20]=[CH:2]/[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:3]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 78373Dimethylformamide dimethyl acetal2×HCID 606426Methyl 5-acetyl-2-methoxybenzoate

Produkt 1

HCID 58015477Methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Methyl 5-acetyl-2-methoxybenzoate (11.98 g, 48.0 mmol) was added to N,N-dimethylformamide dimethyl acetal (44.6 g, 374.5 mmol) held under a nitrogen atmosphere. The resulting solution was heated at 95° C. for 60 minutes. Methanol (10 ml) was then removed by atmospheric distillation and further N,N-dimethylformamide dimethyl acetal (8.90 g, 74.9 mmol) added. The resulting solution was heated at 95° C. for a further 270 minutes. The reaction was then cooled to 50° C. and ethyl acetate (35 mL) added. Solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL) added. Further solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL) added. The reaction mixture is cooled to RT whereby the desired product crystallises out as a granular, free flowing solid. The solid was isolated by filtration, washed twice with fresh ethyl acetate (2×30 mL) and dried to constant weight to afford 11.39 g of the desired methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate (8).

Aufarbeitung

  1. additionadded
  2. temperatureThe resulting solution was heated at 95° C. for a further 270 minutes
  3. temperatureThe reaction was then cooled to 50° C.
  4. customSolvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL)
  5. additionadded
  6. customFurther solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL)
  7. additionadded
  8. temperatureThe reaction mixture is cooled to RT whereby the desired product
  9. customcrystallises out as a granular,
  10. customThe solid was isolated by filtration
  11. washwashed twice with fresh ethyl acetate (2×30 mL)
  12. customdried to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-8e86a24c94064261b40e8b03092a0b64
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198441B2

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