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

HRID 1440381Notes

Reaction equation

HRID 1440381 reaction equation
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

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 11894Methyl 2-bromobenzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 10340Sodium CarbonateSolvent

Procedure

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 aqueous Na2CO3 (60 ml) was heated at 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).

Workup

  1. temperatureat 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

Sources & evidence

ORD record
ord-a24f856616374c8c9579edfaded09a71
Source dataset
uspto-grants-1996_03
Patent number
US05498722

Reaction notes

Loading…