Hydrochloric Acid → Ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoate

HRID 2292133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292133
[H-].[Na+].[CH3:3][C:4]1[N:8]([CH:9](O)[CH3:10])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1.Cl[CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl.[O:27]1CCCC1>>[CH3:3][C:4]1[N:8]([CH2:9][CH2:10][O:27][CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 212769632-Methylbenzimidazol-1-ylethanol

Produkt 1

HCID 20070378Ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoateAusbeute 59 %

Versuchsvorschrift

Sodium hydride (1.46 g, 80% suspension in oil) was suspended in dry tetrahydrofuran (60 ml) under nitrogen. 2-Methylbenzimidazol-1-ylethanol (4.3 g) was added and the suspension was sonicated at 40° C. for 2 hours. Ethyl 4-chloroacetoacetate (4.02 g) in tetrahydrofuran (20 ml) was added dropwise and sonication continued for a further 6 hours. The reaction was poured into 1N hydrochloric acid (50 ml), the tetrahydrofuran was removed under reduced pressure and the aqueous phase washed with toluene. The aqueous phase was adjusted to pH7 with potassium carbonate and extracted with dichloromethane (2×100 ml). The organic extracts were combined, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was chromatographed on silica eluting with 5% methanol in ethyl acetate. The fractions containing the product were combined and evaporated to yield the title compound (4.4 g, 59%) as a red oil.

Aufarbeitung

  1. customthe suspension was sonicated at 40° C. for 2 hours
  2. customsonication
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. washthe aqueous phase washed with toluene
  5. extractionextracted with dichloromethane (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was chromatographed on silica eluting with 5% methanol in ethyl acetate
  9. additionThe fractions containing the product
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-da3e5204aa874315a44e514dcd510bc6
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04801598

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