1,2-Dimethoxyethane → Methyl 2-(5-methyl-2-benzofuranyl)benzoate

HRID 1033558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033558
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO[CH2:14][CH2:15][O:16][CH3:17]>C([O-])([O-])=O.[Na+].[Na+].CCOCC>[CH3:8][C:3]1[CH:4]=[CH:14][C:15]2[O:16][C:17]([C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=3[C:4]([O:6][CH3:7])=[O:5])=[CH:10][C:11]=2[CH:2]=1

Komponenten

5

Edukt 2

HCID 80711,2-DimethoxyethaneHCID 11894Methyl 2-bromobenzoate

Produkt 1

HCID 10378229Methyl 2-(5-methyl-2-benzofuranyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

A solution of methyl 2-bromobenzoate (11.70 g), Intermediate 1 (12.75 g) and tetrakistriphenylphosphine palladium (0) (0.5 g) in DME (300 ml) and 2N Na2CO3 (60 ml) was heated to reflux with vigorous stirring under nitrogen. After 1.5 h a further 500 mg of catalyst was added and stirring at reflux under nitrogen continued. After about 5 h the reaction was cooled to room temperature and diluted with ether (300 ml). The organic layer was separated and washed with water (3×100 ml) and dried. Filtration and evaporation gave a yellow oily suspension (19.27 g) which was purified by chromatography eluting with System A (1:9) to give a yellow oil (11.06 g). This was further purified by Kugelrohr distillation to give the title compound (4.31 g).

Aufarbeitung

  1. temperatureto reflux
  2. stirringstirring
  3. temperatureat reflux under nitrogen
  4. customThe organic layer was separated
  5. washwashed with water (3×100 ml)
  6. customdried
  7. filtrationFiltration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1c5c897965e54c479dc8536b899faff4
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310927

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