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

HRID 1729490ノート

反応式

HRID 1729490 の反応式
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

参加物

5

反応物 2

HCID 80711,2-DimethoxyethaneHCID 11894Methyl 2-bromobenzoate

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a3ed052b5dbb45ec8237aca5b6f6d7fd
出典データセット
uspto-grants-1994_07
特許番号
US05332831

反応ノート

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