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

HRID 1729490Notes

Reaction equation

HRID 1729490 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-a3ed052b5dbb45ec8237aca5b6f6d7fd
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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