Sodium Carbonate → 5-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 2063788노트

반응식

HRID 2063788 반응식
C(B1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])(C)[O:4]1)=C.C(=O)([O-])[O-].[Na+].[Na+].[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2OC(C)(C)[C:24](=O)[C:23]=2[C:30]=1Br>C(OCC)(=O)C.O.COCCOC.C(O)C>[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2[O:7][C:6]([CH3:8])([CH3:9])[C:5](=[O:4])[C:11]=2[C:30]=1[CH:23]=[CH2:24]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 667597955-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

생성물 1

HCID 667591945-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one수율 91%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan (3.79 g, 24.6 mmol), tetrakistriphenyl phosphine palladium (605 mg, 0.523 mmol), sodium carbonate (1.36 g, 12.8 mmol), water (8 mL) and ethanol (5 mL) were added to a solution of DME (14 mL) containing 5-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (2.00 g, 7.04 mmol) synthesized in Reference Example 21, and the mixture was stirred under argon atmosphere at 100° C. for 45 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15) to give 1.47 g of the title compound (yield: 91%).

후처리

  1. customsynthesized in Reference Example 21
  2. temperatureAfter cooled to room temperature
  3. customIt was dried
  4. customAfter that, the solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15)

출처 및 근거

ORD 기록
ord-e0e50aecc7e7477db5b5cb7b36e6d9db
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288390B2

반응 노트

불러오는 중…