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

HRID 1850379노트

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HRID 1850379 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

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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-6425e6d07076452094f84243459d932a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957069B2

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