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

HRID 1033558노트

반응식

HRID 1033558 반응식
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

참가 물질

5

반응물 2

HCID 80711,2-DimethoxyethaneHCID 11894Methyl 2-bromobenzoate

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 10340Sodium Carbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1c5c897965e54c479dc8536b899faff4
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310927

반응 노트

불러오는 중…